Tetrahydrofuran → HCID 67316148, compound

HRID 1014498Notes

Reaction equation

HRID 1014498 reaction equation
[CH3:1][N:2]([CH3:49])[CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:47][CH3:48])=[C:13]([NH:16][C:17]3[N:30]4[C:21](=[N:22][C:23]5[C:28]([C:29]4=[O:31])=[C:27]([F:32])[C:26]([F:33])=[CH:25][CH:24]=5)[C:20]4[CH:34]=[CH:35][N:36]([S:37]([C:40]5[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=5)(=[O:39])=[O:38])[C:19]=4[N:18]=3)[CH:14]=2)C[CH2:8][CH2:7]1)=[O:5].[OH-].[NH4+:51].[CH2:52]1[CH2:56]OC[CH2:53]1>C(OCC)(=O)C>[CH3:1][N:2]([CH3:49])[CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:47][CH3:48])=[C:13]([NH:16][C:17]3[N:30]=[C:21]([NH:22][C:23]4[C:28]([C:29]([NH:51][CH:52]([CH3:56])[CH3:53])=[O:31])=[C:27]([F:32])[C:26]([F:33])=[CH:25][CH:24]=4)[C:20]4[CH:34]=[CH:35][N:36]([S:37]([C:40]5[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=5)(=[O:39])=[O:38])[C:19]=4[N:18]=3)[CH:14]=2)[CH2:8][CH2:7]1)=[O:5]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 67315992HCID 67315992, compound

Product 1

HCID 67316148HCID 67316148, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-{[1-(N,N-dimethylglycyl)-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinyl]amino}-8,9-difluoro-3-[(4-methylphenyl)sulfonyl]pyrrolo[2′,3′:4,5]pyrimido[6,1-b]quinazolin-7(3H)-one (270 mg, 0.393 mmol) in THF (5 mL) was added ammonium hydroxide (27% aqueous) (100 mL, large excess). The resulting mixture was let stir at rt for 16 h at which time it was diluted with ethyl acetate and washed with water and a saturated brine solution. Organics were dried over sodium sulfate and solvents removed under reduced pressure. The residue was purified via chromatography on SiO2 and afforded 6-({2-{[1-(N,N-dimethylglycyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-2,3-difluoro-N-(1-methylethyl)benzamide (110 mg, 0.156 mmol) as a yellow solid. (ESIMS (M+H)+=705)

Workup

  1. washwashed with water
  2. dry with materialOrganics were dried over sodium sulfate and solvents
  3. customremoved under reduced pressure
  4. customThe residue was purified via chromatography on SiO2

Sources & evidence

ORD record
ord-969032471f9744e98879f9ab103fb359
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…