7-amino-1-methyl-4,5-dihydro-3,1-benzoxazepin-2(1H)-one → 2-{5-Chloro-4-[2-(5-methyl-[1,3,4]thiadiazol-2-yl)-phenylamino]-pyrimidin-2-ylamino}-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one

HRID 1041498Notes

Reaction equation

HRID 1041498 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[C:15]2[S:16][C:17]([CH3:20])=[N:18][N:19]=2)[C:5]([Cl:21])=[CH:4][N:3]=1.[NH2:22][C:23]1[CH:24]=[CH:25][C:26]2[N:32]([CH3:33])[C:31](=[O:34])[O:30][CH2:29][CH2:28][C:27]=2[CH:35]=1>>[Cl:21][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[S:16][C:17]([CH3:20])=[N:18][N:19]=2)=[N:7][C:2]([NH:22][C:23]2[CH:24]=[CH:25][C:26]3[N:32]([CH3:33])[C:31](=[O:34])[O:30][CH2:29][CH2:28][C:27]=3[CH:35]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 580154687-amino-1-methyl-4,5-dihydro-3,1-benzoxazepin-2(1H)-oneHCID 86634053(2,5-Dichloro-pyrimidin-4-yl)-[2-(5-methyl-[1,3,4]thiadiazol-2-yl)-phenyl]-amine

Product 1

HCID 668304082-{5-Chloro-4-[2-(5-methyl-[1,3,4]thiadiazol-2-yl)-phenylamino]-pyrimidin-2-ylamino}-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one

Procedure

The title compound was prepared by combining (2,5-dichloro-pyrimidin-4-yl)-[2-(5-methyl-[1,3,4]thiadiazol-2-yl)-phenyl]-amine (Example N?, 75 mg, 0.22 mmol) and 2-amino-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one (Example N?, 47 mg, 0.24 mmol) in an analogous manner described in Example 356c. The title product was isolated as described in Example 1477b as a white powder (32 mg, 26%) and had the following properties: m.p: 174-177° C.; LC/MS (m/e): 494 (M+H); 1H-NMR (DMSO-d6, 400 MHz): δ 10.75 (s, 1H), 9.40 (s, 1H), 8.40-5.06 (series of m, 2H), 8.04 (d, J=7.0, 1H), 7.75-7.30 (series of m, 4H), 7.10 (d, J=8.6, 1H), 4.30 (t, J=6.3, 2H), 3.23 (s, 3H), 2.37 (s, 3H), 2.60 (m, 2H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-303037cd8dc94b73b01c004a6e8124f0
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

Loading…