7-Amino-1-ethyl-8-methoxy-1,3,4,5-tetrahydro-benzo[b]azepin-2-one → 7-[5-Chloro-4-(4-dimethylamino-2-methoxy-phenylamino)-pyrimidin-2-ylamino]-1-ethyl-8-methoxy-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

HRID 1041364Notes

Reaction equation

HRID 1041364 reaction equation
[NH2:1][C:2]1[C:15]([O:16][CH3:17])=[CH:14][C:5]2[N:6]([CH2:12][CH3:13])[C:7](=[O:11])[CH2:8][CH2:9][CH2:10][C:4]=2[CH:3]=1.Cl[C:19]1[N:24]=[C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([N:32]([CH3:34])[CH3:33])=[CH:28][C:27]=2[O:35][CH3:36])[C:22]([Cl:37])=[CH:21][N:20]=1>>[Cl:37][C:22]1[C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([N:32]([CH3:33])[CH3:34])=[CH:28][C:27]=2[O:35][CH3:36])=[N:24][C:19]([NH:1][C:2]2[C:15]([O:16][CH3:17])=[CH:14][C:5]3[N:6]([CH2:12][CH3:13])[C:7](=[O:11])[CH2:8][CH2:9][CH2:10][C:4]=3[CH:3]=2)=[N:20][CH:21]=1

Participants

3

Reactant 2

HCID 672644367-Amino-1-ethyl-8-methoxy-1,3,4,5-tetrahydro-benzo[b]azepin-2-oneHCID 86634017N(1)-(2,5-Dichloro-pyrimidin-4-yl)-2-methoxy-N(4),N(4)-dimethyl-benzene-1,4-diamine

Product 1

HCID 672643747-[5-Chloro-4-(4-dimethylamino-2-methoxy-phenylamino)-pyrimidin-2-ylamino]-1-ethyl-8-methoxy-1,3,4,5-tetrahydro-benzo[b]azepin-2-oneYield 72.4%

Procedure

Following a procedure analogous to Example 113, 7-Amino-1-ethyl-8-methoxy-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (55 mgs) and N(1)-(2,5-Dichloro-pyrimidin-4-yl)-2-methoxy-N(4),N(4)-dimethyl-benzene-1,4-diamine (66 mgs) were converted to the title compound (78 mgs) as a white solid. 1H-NMR (CDCl3, 400 MHz): 8.20 (s, 1H), 8.02 (s, 1H), 7.95 (d, J=8.3 Hz, 1H), 7.53 (s, 1H), 6.69 (s, 1H), 6.37-6.35 (m, 2H), 4.35-3.8 (broad absorption, 2H), 3.90 (d, J=7.3 Hz, 6H) 2.98 (d, J=0.8 Hz, 3H), 2.65-2.50 (m, 1H), 2.30-2.00 (m, 3H), 1.6 (broad s, 2H), 1.15 (t, J=7.0 Hz, 3H); LC/MS: found (M+H)+=511.46 MP: 183-185° C.

Sources & evidence

ORD record
ord-b6e918f5951d48508d0e4256255baacf
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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