Methylamine → HCID 59441868, compound

HRID 1014541Notes

Reaction equation

HRID 1014541 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]=[CH:20][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.[CH3:32][N:33]([CH2:35][C:36]([N:38]1[C:47]2[C:42](=[CH:43][C:44]([CH3:49])=[C:45]([NH2:48])[CH:46]=2)[CH2:41][CH2:40][CH2:39]1)=[O:37])[CH3:34].[CH3:50][NH2:51]>C1COCC1>[CH3:34][N:33]([CH3:32])[CH2:35][C:36]([N:38]1[C:47]2[C:42](=[CH:43][C:44]([CH3:49])=[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]([NH:51][CH3:50])=[O:17])[C:6]4[CH:19]=[CH:20][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][CH2:39]1)=[O:37]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 59442100HCID 59442100, compoundHCID 673162535-chloro-8-fluoro-3-[(4-methylphenyl)sulfonyl]pyrrolo[2',3':4,5]pyrimido[6,1-b]quinazolin-7(3H)-one HCl salt

Product 1

HCID 59441868HCID 59441868, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A slurry of 5-chloro-8-fluoro-3-[(4-methylphenyl)sulfonyl]pyrrolo[2′,3′:4,5]pyrimido[6,1-b]quinazolin-7(3H)-one hydrogen chloride (300 mg, 0.626 mmol) and 1-[(dimethylamino)acetyl]-6-methyl-1,2,3,4-tetrahydro-7-quinolinamine (155 mg, 0.626 mmol) in THF (50 mL) was heated at 70° C. for 20 h. The resulting mixture was allowed to cool to rt and was treated with a 2M MeNH2 solution in THF (10 mL). The reaction mixture was stirred at rt for 3 days, then concentrated onto Celite and purified by silica gel chromatography using 1-20% MeOH (containing 0.2% NH3)/CH2Cl2 to afford 2-({2-{[1-(N,N-dimethylglycyl)-6-methyl-1,2,3,4-tetrahydro-7-quinolinyl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluoro-N-methylbenzamide (87 mg, 20%). ESIMS (M+H)+=685.18.

Workup

  1. concentrationconcentrated onto Celite
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-ee0a8e83c50248d5865e393a71590cd2
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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