Methylamine → HCID 67316507, compound

HRID 1014500Notes

Reaction equation

HRID 1014500 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)[CH2:9][CH2:8][CH2:7]1)=[O:5].[CH3:50][NH2:51]>C1COCC1.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][CH3:50])=[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:38])=[O:39])[C:19]=4[N:18]=3)[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:5]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 67315992HCID 67315992, compound

Product 1

HCID 67316507HCID 67316507, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 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 (50 mL) was added methyl amine (2M solution in THF) (1.96 mL, 3.93 mmol). The resulting mixture was let stir at rt for 1 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)-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinyl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-2,3-difluoro-N-methylbenzamide (139 mg, 0.193 mmol) as a yellow solid. (ESIMS (M+H)+=719)

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-537c4784feac45878057abb2496214fe
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…