2-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamide → HCID 66829628, compound

HRID 1041507Notes

Reaction equation

HRID 1041507 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[C:5]([Cl:19])=[CH:4][N:3]=1.[NH2:20][C:21]1[C:33]([O:34][CH3:35])=[CH:32][C:24]2[CH2:25][CH2:26][O:27][C:28](=[O:31])[N:29]([CH3:30])[C:23]=2[CH:22]=1>>[Cl:19][C:5]1[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])=[N:7][C:2]([NH:20][C:21]2[C:33]([O:34][CH3:35])=[CH:32][C:24]3[CH2:25][CH2:26][O:27][C:28](=[O:31])[N:29]([CH3:30])[C:23]=3[CH:22]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 579741322-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamideHCID 67264099HCID 67264099, compound

Product 1

HCID 66829628HCID 66829628, compoundYield 20%

Procedure

In an analogous manner to Example 1503, the product was prepared from 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide and 3-Amino-2-methoxy-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one. Product isolated as a white solid (20 mg, 20%). mp: 256-258° C., MS (ESI+): 483 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 11.02 (s, 1H), 8.53 (s, J=8 Hz, 1H), 8.34 (s, 1H), 8.15 (s, 1H), 7.51 (d, J=7 Hz, 1H), 7.42 (t, J=7 Hz, 1H), 7.15 (t, J=7 Hz, 1H), 6.73 (s, 1H), 6.26 (br s, 1H), 4.53 (t, 7 Hz, 2H), 3.94 (s, 1H), 3.06 (d, J=5 Hz, 3H), 3.02 (s, 3H), 2.94 (t, J=7, 2H).

Sources & evidence

ORD record
ord-f26dd48020304d648432a6242341a78e
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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