7-amino-1-methyl-4,5-dihydro-3,1-benzoxazepin-2(1H)-one → 2-{5-Chloro-4-[2-fluoro-6-(tetrahydro-furan-3-yloxy)-phenoxy]-pyrimidin-2-ylamino}-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one

HRID 1041341Notes

Reaction equation

HRID 1041341 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[C:14]([O:15][CH:16]3[CH2:20][CH2:19][O:18][CH2:17]3)=[CH:13][CH:12]=[CH:11][C:10]=2[F:21])[C:5]([Cl:22])=[CH:4][N:3]=1.[NH2:23][C:24]1[CH:25]=[CH:26][C:27]2[N:33]([CH3:34])[C:32](=[O:35])[O:31][CH2:30][CH2:29][C:28]=2[CH:36]=1>>[Cl:22][C:5]1[C:6]([O:8][C:9]2[C:14]([O:15][CH:16]3[CH2:20][CH2:19][O:18][CH2:17]3)=[CH:13][CH:12]=[CH:11][C:10]=2[F:21])=[N:7][C:2]([NH:23][C:24]2[CH:25]=[CH:26][C:27]3[N:33]([CH3:34])[C:32](=[O:35])[O:31][CH2:30][CH2:29][C:28]=3[CH:36]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 580154687-amino-1-methyl-4,5-dihydro-3,1-benzoxazepin-2(1H)-oneHCID 866340112,5-Dichloro-4-[2-fluoro-6-(tetrahydro-furan-3-yloxy)-phenoxy]-pyrimidine

Product 1

HCID 668295972-{5-Chloro-4-[2-fluoro-6-(tetrahydro-furan-3-yloxy)-phenoxy]-pyrimidin-2-ylamino}-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one

Procedure

2-{5-Chloro-4-[2-fluoro-6-(tetrahydro-furan-3-yloxy)-phenoxy]-pyrimidin-2-ylamino}-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one was prepared from 2,5-Dichloro-4-[2-fluoro-6-(tetrahydro-furan-3-yloxy)-phenoxy]-pyrimidine and 2-Amino-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one in an analogous manner to Example 1221d. Title compound was isolated as a white solid HPLC purity=99%, LCMS 503.21 (M+H), 1H-NMR (DMSO-d6, 400 MHz) δ 9.88 (s, 1H), 8.52 (s, 1H), 7.30-7.18 (m, 5H), 7.02 (d, J=8.7 Hz, 1H), 4.87 (s, 1H), 4.26-4.23 (m, 2H), 3.69-3.65 (m, 4H), 3.19 (s, 3H), 2.65 (m, 2H), 1.94-1.90 (m, 2H).

Sources & evidence

ORD record
ord-0969b8365b264f4a96279ff43cd5a4a0
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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