HCID 67264508, compound → HCID 67264577, compound

HRID 1687368Notes

Reaction equation

HRID 1687368 reaction equation
[NH2:1][C:2]1[C:3]([O:17][CH3:18])=[CH:4][C:5]2[CH2:11][N:10]([CH2:12][CH3:13])[CH2:9][C:8](=[O:14])[N:7]([CH3:15])[C:6]=2[CH:16]=1.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>>[Cl:38][C:23]1[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])=[N:25][C:20]([NH:1][C:2]2[C:3]([O:17][CH3:18])=[CH:4][C:5]3[CH2:11][N:10]([CH2:12][CH3:13])[CH2:9][C:8](=[O:14])[N:7]([CH3:15])[C:6]=3[CH:16]=2)=[N:21][CH:22]=1

Participants

3

Reactant 2

HCID 67264508HCID 67264508, compoundHCID 86633854N-[(1R,2R)-2-(2,5-dichloropyrimidin-4-ylamino)-cyclohexyl]-methanesulfonamide

Product 1

HCID 67264577HCID 67264577, compound

Procedure

The title compound was prepared from 8-Amino-4-ethyl-7-methoxy-1-methyl-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one and N-[(1R,2R)-2-(2,5-Dichloro-pyrimidin-4-ylamino)-cyclohexyl]-methanesulfonamide in an analogous manner to example 730 (0.062 g, 46%) Mp 214-216° C.; LCMS (m/e) 552 (M); 1H-NMR (DMSO, 400 MHz) δ 8.23 (s, 1H), 7.97 (s, 1H), 7.74 (s, 1H), 7.22-7.20 (d, 1H, J=8.84 Hz), 7.04 (s, 1H), 6.88-6.86 (d, 1H, J=8.34 Hz), 3.89 (s, 3H), 3.88-3.79 (m, 1H), 3.50 (s, 2H), 3.28 (s, 3H), 2.99 (s, 2H), 2.89 (s, 3H), 2.58-2.53 (q, 2H, J=6.82 Hz), 2.05-1.90 (m, 2H), 1.68-1.58 (m, 2H), 1.40-1.17 (m, 3H), 1.08-1.04 (t, 3H, J=7.33 Hz).

Sources & evidence

ORD record
ord-1d30657e344b4dd1afffd5158baafdcd
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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