Methanol → 3-[5-chloro-2-(1-ethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamino)-pyrimidin-4-ylamino]-thiophene-2-carboxylic acid methylamide
Reaction equation
[CH3:1][NH:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][C:11]1[C:16]([Cl:17])=[CH:15][N:14]=[C:13]([NH:18][C:19]2[CH:20]=[CH:21][C:22]3[CH2:28][N:27](C(=O)C)[CH2:26][C:25](=[O:32])[N:24]([CH2:33][CH3:34])[C:23]=3[CH:35]=2)[N:12]=1)=[O:4].C(Cl)Cl.CO>CN.O.CN.C1COCC1>[CH3:1][NH:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][C:11]1[C:16]([Cl:17])=[CH:15][N:14]=[C:13]([NH:18][C:19]2[CH:20]=[CH:21][C:22]3[CH2:28][NH:27][CH2:26][C:25](=[O:32])[N:24]([CH2:33][CH3:34])[C:23]=3[CH:35]=2)[N:12]=1)=[O:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 3-[2-(4-acetyl-1-ethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamino)-5-chloro-pyrimidin-4-ylamino]-thiophene-2-carboxylic acid methylamide (157 mg, 0.3 mmol) in 12 mL of 40% methylamine/water and 3 mL of 2M methylamine/THF) was heated in a sealed tube at 120° C. for 16 hours. Chromatography of the concentrated residue on TLC plates with methylene chloride and methanol (100:9) gave 43 mg of 3-[5-chloro-2-(1-ethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamino)-pyrimidin-4-ylamino]-thiophene-2-carboxylic acid methylamide (29%): 1H NMR (300 MHz, CD3OD) δ 8.42 (d, 1H), 8.1 (s, 1H), 7.88 (s, 1H), 7.45 (m, 2H), 7.33 (d, 1H), 3.92 (m, 4H), 3.35 (s, 2H), 2.9 (s, 3H), 1.18 (t, 3H); MS (m/e): 472.1 (M+1).
Sources & evidence
- ORD record
- ord-8469de67492c42a7b526d6ffb3aba5b8
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148391B2
Reaction notes
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