HCID 67263871, compound → HCID 66830640, compound

HRID 1688110Notes

Reaction equation

HRID 1688110 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][C:9](=[O:12])[N:8]([CH3:13])[CH2:7][C:6]=2[CH:14]=1.Cl[C:16]1[N:21]=[C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:29][NH:30][CH3:31])[C:19]([Cl:32])=[CH:18][N:17]=1>>[Cl:32][C:19]1[C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:29][NH:30][CH3:31])=[N:21][C:16]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[CH2:11][CH2:10][C:9](=[O:12])[N:8]([CH3:13])[CH2:7][C:6]=3[CH:14]=2)=[N:17][CH:18]=1

Participants

3

Reactant 2

HCID 67263871HCID 67263871, compoundHCID 86634085HCID 86634085, compound

Product 1

HCID 66830640HCID 66830640, compound

Procedure

Following a procedure analogous to Example 1741e, 8-amino-2-methyl-1,2,4,5-tetrahydro-benzo[c]azepin-3-one and (2,5-dichloro-pyrimidin-4-yl)-(2-methylaminomethyl-phenyl)-amine (TFA salt) was converted to 8-[5-chloro-4-(2-methylaminomethyl-phenylamino)-pyrimidin-2-ylamino]-2-methyl-1,2,4,5-tetrahydro-benzo[c]azepin-3-one. HCl salt: 1H NMR (300 MHz, CD3OD) δ 8.18 (s, 1H), 7.6 (m, 3H), 7.52 (d, 1H), 7.1 (m, 3H), 4.41 (s, 2H), 4.18 (s, 2H), 3.07 (t, 2H), 2.97 (s, 3H), 2.89 (t, 2H), 2.65 (s, 3H); MS (m/e) 437 (M+1).

Sources & evidence

ORD record
ord-ecc96df05b0044a99cbfbfff6128cfa2
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

Loading…