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Ammonium Hydroxide → 2-({2-{[1-(N,N-dimethylglycyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-6-methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzamide

HRID 1014567
Notes
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Reaction equation

HRID 1014567 reaction equation
Cl.Cl[C:3]1[N:16]2[C:7](=[N:8][C:9]3[C:14]([C:15]2=[O:17])=[C:13]([F:18])[CH:12]=[CH:11][CH:10]=3)[C:6]2[CH:19]=[C:20]([CH3:32])[N:21]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[C:5]=2[N:4]=1.[CH3:33][N:34]([CH2:36][C:37]([N:39]1[C:47]2[C:42](=[CH:43][C:44]([O:49][CH3:50])=[C:45]([NH2:48])[CH:46]=2)[CH2:41][CH2:40]1)=[O:38])[CH3:35].[OH-].[NH4+:52]>FC(F)(F)CO.C(OCC)(=O)C>[CH3:35][N:34]([CH3:33])[CH2:36][C:37]([N:39]1[C:47]2[C:42](=[CH:43][C:44]([O:49][CH3:50])=[C:45]([NH:48][C:3]3[N:16]=[C:7]([NH:8][C:9]4[CH:10]=[CH:11][CH:12]=[C:13]([F:18])[C:14]=4[C:15]([NH2:52])=[O:17])[C:6]4[CH:19]=[C:20]([CH3:32])[N:21]([S:22]([C:25]5[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=5)(=[O:24])=[O:23])[C:5]=4[N:4]=3)[CH:46]=2)[CH2:41][CH2:40]1)=[O:38]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 534147641-(6-Amino-5-methoxy-2,3-dihydro-1H-indol-1-yl)-2-(dimethylamino)ethan-1-oneHCID 673158975-chloro-8-fluoro,2-methyl-3-[(4-methylphenyl)sulfonyl]pyrrolo[2',3':4,5]pyrimido[6,1-b]quinazolin-7(3H)-one HCl salt

Product 1

HCID 673164142-({2-{[1-(N,N-dimethylglycyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-6-methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzamide

Reagents, catalysts & solvents 2

HCID 64092,2,2-TrifluoroethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a flask containing 5-chloro-8-fluoro,2-methyl-3-[(4-methylphenyl)sulfonyl]pyrrolo[2′,3′:4,5]pyrimido[6,1-b]quinazolin-7(3H)-one HCl salt (423 mg, 0.86 mmol) in 2,2,2-trifluoroethanol (10 mL) was added 1-[(dimethylamino)acetyl]-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine (254 mg, 1.02 mmol). The resulting slurry was stirred at 80° C. for 6 h. Solvents were removed under reduced pressure to afford a yellow solid. One third of this material (˜200 mg) was suspended in THE (5 mL) and excess aqueous ammonium hydroxide (27%) (˜12 mL) was added. The reaction was let stir at rt for 5 h, at which time the reaction mixture was diluted with ethyl acetate and washed with water and saturated brine solution. Organics were dried over sodium sulfate and solvents removed under reduced pressure to afford a yellow solid that was purified via chromatography on SiO2 to afford 2-({2-{[1-(N,N-dimethylglycyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-6-methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzamide (117 mg, 0.17 mmol) as a yellow solid. ESIMS (M+H)+=688.

Workup

  1. customSolvents were removed under reduced pressure
  2. customto afford a yellow solid
  3. additionwas added
  4. stirringThe reaction was let stir at rt for 5 h, at which time the reaction mixture
  5. washwashed with water and saturated brine solution
  6. dry with materialOrganics were dried over sodium sulfate and solvents
  7. customremoved under reduced pressure
  8. customto afford a yellow solid
  9. customthat was purified via chromatography on SiO2

Sources & evidence

ORD record
ord-08519c1a5ef8460c9000e86ae1c5378a
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07981903B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes