Methylamine → HCID 59441741, compound

HRID 1014520Notes

Reaction equation

HRID 1014520 reaction equation
[CH3:1][N:2]([CH3:48])[CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:46][CH3:47])=[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])[CH:26]=[CH:25][CH:24]=5)[C:20]4[CH:33]=[CH:34][N:35]([S:36]([C:39]5[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=5)(=[O:38])=[O:37])[C:19]=4[N:18]=3)[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:5].[CH3:49][NH2:50]>C1COCC1>[CH3:1][N:2]([CH3:48])[CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:46][CH3:47])=[C:13]([NH:16][C:17]3[N:30]=[C:21]([NH:22][C:23]4[CH:24]=[CH:25][CH:26]=[C:27]([F:32])[C:28]=4[C:29]([NH:50][CH3:49])=[O:31])[C:20]4[CH:33]=[CH:34][N:35]([S:36]([C:39]5[CH:40]=[CH:41][C:42]([CH3:45])=[CH:43][CH:44]=5)(=[O:38])=[O:37])[C:19]=4[N:18]=3)[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:5]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59441862HCID 59441862, compound

Product 1

HCID 59441741HCID 59441741, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-{[1-(N,N-dimethylglycyl)-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinyl]amino}-8-fluoro-3-[(4-methylphenyl)sulfonyl]pyrrolo[2′,3′:4,5]pyrimido[6,1-b]quinazolin-7(3H)-one (5.0 g, 7.47 mmol) in THF (200 ml) was added 2.0 M methylamine in THF (74.7 ml, 149 mmol) and the resulting reaction was stirred overnight at rt. The crude reaction was adsorbed to silica gel and purified by LC (DCM to 5% MeOH/DCM) to give 2-({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)-6-fluoro-N-methylbenzamide (3.2 g, 61%). ESIMS (M+H)+=701.

Workup

  1. customthe resulting reaction
  2. customThe crude reaction
  3. custompurified by LC (DCM to 5% MeOH/DCM)

Sources & evidence

ORD record
ord-801c5033d31c448f8b5b0e8315c14acb
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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