2-Amino-3-methoxy-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one → 2-[5-Chloro-4-(2-methoxy-phenylamino)-pyrimidin-2-ylamino]-3-methoxy-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one

HRID 1041504Notes

Reaction equation

HRID 1041504 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])[C:5]([Cl:17])=[CH:4][N:3]=1.[NH2:18][C:19]1[C:20]([O:32][CH3:33])=[CH:21][C:22]2[N:28]([CH3:29])[C:27](=[O:30])[O:26][CH2:25][CH2:24][C:23]=2[CH:31]=1>>[Cl:17][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[N:7][C:2]([NH:18][C:19]2[C:20]([O:32][CH3:33])=[CH:21][C:22]3[N:28]([CH3:29])[C:27](=[O:30])[O:26][CH2:25][CH2:24][C:23]=3[CH:31]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 672646482-Amino-3-methoxy-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-oneHCID 79633486(2,5-Dichloro-pyrimidin-4-yl)-(2-methoxy-phenyl)-amine

Product 1

HCID 668298102-[5-Chloro-4-(2-methoxy-phenylamino)-pyrimidin-2-ylamino]-3-methoxy-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-oneYield 69%

Procedure

In an analogous manner to Example 1503, the product was prepared from (2,5-Dichloro-pyrimidin-4-yl)-(2-methoxy-phenyl)-amine and 2-Amino-3-methoxy-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one. Product isolated as a white solid (70 mg, 69%). mp: 192-194° C., MS (ESI+): 456 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 8.24 (s, 1H), 8.12 (s, 1H), 7.96 (d, 1H), 7.63 (s, 1H), 7.14 (q, 1H), 7.13 (s, 1H), 6.99 (s, 1H), 6.92 (t, 1H), 4.27 (t, J=6 Hz, 2H), 3.82 (s, 6H), 3.28 (s, 3H), 2.69 (t, J=6 Hz, 2H).

Sources & evidence

ORD record
ord-bfe8e56ed1714003b6df0d2b190ad4d9
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

Loading…