2-Methoxy-4-morpholinoaniline → 2-Methoxy-3-[4-(2-methoxy-4-morpholin-4-yl-phenylamino)-5-trifluoromethyl-pyrimidin-2-ylamino]-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one

HRID 1041513

Reaction equation

HRID 1041513 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[C:25]([O:26][CH3:27])=[CH:24][C:16]3[CH2:17][CH2:18][O:19][C:20](=[O:23])[N:21]([CH3:22])[C:15]=3[CH:14]=2)[N:3]=1.[CH3:28][O:29][C:30]1[CH:35]=[C:34]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)[CH:33]=[CH:32][C:31]=1[NH2:42]>>[CH3:27][O:26][C:25]1[C:13]([NH:12][C:4]2[N:3]=[C:2]([NH:42][C:31]3[CH:32]=[CH:33][C:34]([N:36]4[CH2:37][CH2:38][O:39][CH2:40][CH2:41]4)=[CH:35][C:30]=3[O:29][CH3:28])[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=2)=[CH:14][C:15]2[N:21]([CH3:22])[C:20](=[O:23])[O:19][CH2:18][CH2:17][C:16]=2[CH:24]=1

Participants

3

Reactant 2

HCID 4149602-Methoxy-4-morpholinoanilineHCID 866340553-(4-Chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-2-methoxy-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one

Product 1

HCID 668306902-Methoxy-3-[4-(2-methoxy-4-morpholin-4-yl-phenylamino)-5-trifluoromethyl-pyrimidin-2-ylamino]-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-oneYield 43%

Procedure

In an analogous manner to Example 1513, the product was prepared from 3-(4-Chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-2-methoxy-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one and 2-Methoxy-4-morpholin-4-yl-phenylamine. Product was isolated as a white solid (55 mg, 43%). mp: 221-223° C., MS (ESI+): 575 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 8.38 (s, 1H), 8.30 (s, 1H), 7.83 (s, 1H), 7.68 (s, 1H), 7.60 (br d, 1H), 7.03 (s, 1H), 6.63 (s, 1H), 6.32 (br d, 1H), 4.36 (t, J=6 Hz, 2H), 3.82 (s, 3H), 3.78 (s, 3H), 3.75 (m, 4H), 3.11 (m, 4H), 3.01 (s, 3H), 2.93 (t, J=6 Hz, 2H).

Sources & evidence

ORD record
ord-091e092be6a24ba5a11d6805457c4ccd
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Linked notes

Loading…