2-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamide → HCID 25158500, compound

HRID 1687852Notes

Reaction equation

HRID 1687852 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:26]2[CH2:27][CH2:28][O:29][C:30](=[O:33])[N:31]([CH3:32])[C:25]=2[CH:24]=[CH:23][C:22]=1[O:34][CH3:35]>>[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:26]3[CH2:27][CH2:28][O:29][C:30](=[O:33])[N:31]([CH3:32])[C:25]=3[CH:24]=[CH:23][C:22]=2[O:34][CH3:35])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 579741322-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamideHCID 67263576HCID 67263576, compound

Product 1

HCID 25158500HCID 25158500, compoundYield 4%

Procedure

In an analogous manner to Example 1513, the product was prepared from 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide and 1-Amino-2-methoxy-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one. Product was isolated as a light yellow solid (4.0 mg, 4%). mp: 160° C. followed by solidification and melt at 250 and discoloration, MS (ESI+): 483 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 11.21 (s, 1H), 8.35 (br s, 1H), 8.06 (s, 1H), 7.44 (d, J=8 Hz, 1H), 7.20 (br s, 1H), 7.12 (d, J=8 Hz, 1H), 7.01 (t, 1H), 6.98 (d, J=7 Hz, 1H), 6.40 (s, 1H), 6.21 (br s, 1H), 4.39 (t, 2H), 3.83 (s, 3H), 3.42 (s, 3H), 3.04 (d, J=5 Hz, 3H), 2.98 (t, J=6 Hz, 2H).

Sources & evidence

ORD record
ord-c73f8cc01a9d407d99760f20691b6b1b
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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