8-amino-4-methyl-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one → 2[5-chloro-2-(4-methyl-5-oxo-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-8-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide

HRID 1040933Notes

Reaction equation

HRID 1040933 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6](=[O:12])[N:7]([CH3:11])[CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1.Cl[C:16]1[N:21]=[C:20]([NH:22][C:23]2[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=2[C:25]([NH:27][CH3:28])=[O:26])[C:19]([Cl:33])=[CH:18][N:17]=1>>[Cl:33][C:19]1[C:20]([NH:22][C:23]2[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=2[C:25]([NH:27][CH3:28])=[O:26])=[N:21][C:16]([NH:1][C:2]2[CH:14]=[CH:13][C:5]3[C:6](=[O:12])[N:7]([CH3:11])[CH2:8][CH2:9][O:10][C:4]=3[CH:3]=2)=[N:17][CH:18]=1

Participants

3

Reactant 2

HCID 578538918-amino-4-methyl-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-oneHCID 579741322-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamide

Product 1

HCID 668300912[5-chloro-2-(4-methyl-5-oxo-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-8-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamideYield 41%

Procedure

Following the procedure of 512f, 8-amino-4-methyl-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one (0.04 g, 0.0002 mol) and 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl benzamide (0.062 g, 0.0002 mol) were reacted giving 2[5-chloro-2-(4-methyl-5-oxo-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-8-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide (0.037 g, 41%) as a white solid. MP: 288-9° C.; 1H-NMR (DMSO-d6) δ 11.62 (s, 1H), 9.74 (s, 1H), 8.78 (d, 1H), 8.70-2 (d, 1H), 8.29 9s, 1H), 7.75-7 (d, 1H), 7.53-8 (m, 3H), 7.35-8 (d, 1H), 7.17-9 (t, 1H), 4.32-4 (m, 2H), 3.06 (s, 3H), 2.80-1 (d, 3H); LC/MS (ESI+): 453 (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-2f773420216542b791f39f9a3d7e9aa4
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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