HCID 67264420, compound → HCID 67264439, compound

HRID 1687950Notes

Reaction equation

HRID 1687950 reaction equation
[C:1]([N:4]1[CH2:10][C:9]2[CH:11]=[C:12]([O:16][CH3:17])[C:13]([NH2:15])=[CH:14][C:8]=2[NH:7][C:6](=[O:18])[CH2:5]1)(=[O:3])[CH3:2].Cl[C:20]1[N:25]=[C:24]([NH:26][C@@H:27]2[CH2:32][CH2:31][CH2:30][CH2:29][C@H:28]2[NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:23]([Cl:38])=[CH:22][N:21]=1>CO.C(Cl)Cl>[C:1]([N:4]1[CH2:10][C:9]2[CH:11]=[C:12]([O:16][CH3:17])[C:13]([NH:15][C:20]3[N:25]=[C:24]([NH:26][C@@H:27]4[CH2:32][CH2:31][CH2:30][CH2:29][C@H:28]4[NH:33][S:34]([CH3:37])(=[O:35])=[O:36])[C:23]([Cl:38])=[CH:22][N:21]=3)=[CH:14][C:8]=2[NH:7][C:6](=[O:18])[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67264420HCID 67264420, compoundHCID 86633854N-[(1R,2R)-2-(2,5-dichloropyrimidin-4-ylamino)-cyclohexyl]-methanesulfonamide

Product 1

HCID 67264439HCID 67264439, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

In an analogous manner to procedure 1656g, 4-acetyl-8-amino-7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (60 mg, 0.24 mmol) and N-[(1R,2R)-2-(2,5-dichloro-pyrimidin-4-ylamino)-cyclohexyl]-methanesulfonamide (82 mg, 0.24 mmol) were coupled to provide N-{(1R,2R)-2-[2-(4-Acetyl-7-methoxy-2-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]di-azepin-8-ylamino)-5-chloro-pyrimidin-4-ylamino]-cyclohexyl}-methanesulfonamide (14 mg, 10%) as a pale yellow solid following preparative tlc (10% MeOH-DCM); 1H NMR (400 MHz, DMSO-d6) δ 8.23 (s, 1H), 8.15 (s, 1H), 8.00 (s, 1H), 7.47 (s, 1H), 6.73 (s, 1H), 5.63 (d, J=7 Hz, 1H), 5.46 (d, J=7 Hz, 1H), 4.00 (s, 2H), 3.92 (s, 3H), 3.53 (s, 2H), 3.29 (m, 1H), 2.89 (s, 3H), 2.21 (m, 2H), 2.17 (s, 3H), 1.83 (m, 2H), 1.65 (m, 1H), 1.38 (m, 2H), 1.25 (m, 2H); MS (m/e) 553 (M+1); mp 167° C. (dec.).

Sources & evidence

ORD record
ord-3fecf5ecf35d4ef2910d6434613bf520
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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