HCID 67263741, compound → HCID 67264265, compound

HRID 1041613Notes

Reaction equation

HRID 1041613 reaction equation
[NH2:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][C:5]2[CH2:11][N:10]([CH2:12][CH3:13])[CH2:9][C:8](=[O:14])[NH:7][C:6]=2[CH:15]=1.Cl[C:19]1[N:24]=[C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[CH:28][C:27]=2[O:38][CH3:39])[C:22]([Cl:40])=[CH:21][N:20]=1>>[Cl:40][C:22]1[C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([N:32]3[CH2:33][CH2:34][O:35][CH2:36][CH2:37]3)=[CH:28][C:27]=2[O:38][CH3:39])=[N:24][C:19]([NH:1][C:2]2[C:3]([O:16][CH3:17])=[CH:4][C:5]3[CH2:11][N:10]([CH2:12][CH3:13])[CH2:9][C:8](=[O:14])[NH:7][C:6]=3[CH:15]=2)=[N:20][CH:21]=1

Participants

3

Reactant 2

HCID 67263741HCID 67263741, compoundHCID 86633851(2,5-Dichloropyrimidin-4-yl)-(2-methoxy-4-morpholin-4-yl-phenyl)-amine

Product 1

HCID 67264265HCID 67264265, compoundYield 27.7%

Procedure

In an analogous manner to procedure 1656g, 8-amino-4-ethyl-7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (100 mg, 0.43 mmol) and (2,5-dichloro-pyrimidin-4-yl)-(2-methoxy-4-morpholin-4-yl-phenyl)-amine (151 mg, 0.43 mmol) were coupled to provide 8-[5-chloro-4-(2-methoxy-4-morpholin-4-yl-phenylamino)-pyrimidin-2-ylamino]-4-ethyl-7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (66 mg, 22%) as a pale yellow foam following flash chromatography on silica gel (0-5% MeOH-DCM); NMR (400 MHz, CDCl3) δ 8.20 (s, 1H), 8.03 (m, 1H), 7.64 (s, 1H), 7.39 (s, 1H), 7.20 (s, 1H), 6.80 (s, 1H), 6.60 (m, 2H), 3.92 (m, 10H), 3.73 (s, 2H), 3.40 (s, 2H), 3.29 (m, 4H), 2.78 (t, J=7 Hz, 2H), 1.20 (t, J=7 Hz, 3H); MS (m/e) 554 (M+1).

Sources & evidence

ORD record
ord-ffec9a9181724251b38cb858b2def0b8
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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