2-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamide → 2-[5-Chloro-2-(3-prop-2-ynyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide

HRID 1040819Notes

Reaction equation

HRID 1040819 reaction equation
[CH2:1]([N:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[C:12]([NH2:15])[CH:13]=[CH:14][C:7]=2[CH2:6][CH2:5]1)[C:2]#[CH:3].Cl[C:17]1[N:22]=[C:21]([NH:23][C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([NH:28][CH3:29])=[O:27])[C:20]([Cl:34])=[CH:19][N:18]=1>>[Cl:34][C:20]1[C:21]([NH:23][C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([NH:28][CH3:29])=[O:27])=[N:22][C:17]([NH:15][C:12]2[CH:13]=[CH:14][C:7]3[CH2:6][CH2:5][N:4]([CH2:1][C:2]#[CH:3])[CH2:10][CH2:9][C:8]=3[CH:11]=2)=[N:18][CH:19]=1

Participants

3

Reactant 2

HCID 579741322-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamideHCID 866338783-prop-2-ynyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine

Product 1

HCID 866338802-[5-Chloro-2-(3-prop-2-ynyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide

Procedure

2-[5-Chloro-2-(3-prop-2-ynyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide was prepared from 3-prop-2-ynyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine and 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide in an analogous manner to Example 318b. Product isolated as a yellow solid (26 mg, 13%). m.p.=223-225° C.; LCMS (m/e) 461 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 11.07 (s, 1H), 8.67 (d, 1H, J=8.5 Hz), 8.11 (s, 1H), 7.58-7.45 (m, 2H), 7.38 (s, 1H), 7.15-7.05 (m, 2H), 6.89 (s, 1H), 6.30-6.15 (m, 1H), 3.46 (s, 2H), 3.05 (d, 3H, J=4.8 Hz), 2.98-2.87 (m, 4H), 2.80-2.70 (m, 4H), 2.24-2.20 (m, 1H), 2.20-2.17 (m, 1H).

Sources & evidence

ORD record
ord-031c04c12690492eaa4b74eb94e79133
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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