(2,5-Dichloro-pyrimidin-4-yl)-[2-(1-methyl-1H-imidazol-2-yl)-phenyl]-amine → 5-Chloro-N*2*-[7-(2,2-difluoro-ethylamino)-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl]-N*4*-[2-(1-methyl-1H-imidazol-2-yl)-phenyl]-pyrimidine-2,4-diamine

HRID 1040993Notes

Reaction equation

HRID 1040993 reaction equation
[F:1][CH:2]([F:17])[CH2:3][NH:4][CH:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([NH2:16])[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1.Cl[C:19]1[N:24]=[C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]2[N:33]([CH3:37])[CH:34]=[CH:35][N:36]=2)[C:22]([Cl:38])=[CH:21][N:20]=1>>[Cl:38][C:22]1[C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]2[N:33]([CH3:37])[CH:34]=[CH:35][N:36]=2)=[N:24][C:19]([NH:16][C:13]2[CH:14]=[CH:15][C:8]3[CH2:7][CH2:6][CH:5]([NH:4][CH2:3][CH:2]([F:17])[F:1])[CH2:11][CH2:10][C:9]=3[CH:12]=2)=[N:20][CH:21]=1

Participants

3

Reactant 2

HCID 86633891(2,5-Dichloro-pyrimidin-4-yl)-[2-(1-methyl-1H-imidazol-2-yl)-phenyl]-amineHCID 131729566N*7*-(2,2-Difluoro-ethyl)-6,7,8,9-tetrahydro-5H-benzocycloheptene-2,7-diamine

Product 1

HCID 1317295685-Chloro-N*2*-[7-(2,2-difluoro-ethylamino)-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl]-N*4*-[2-(1-methyl-1H-imidazol-2-yl)-phenyl]-pyrimidine-2,4-diamineYield 29%

Procedure

In an analogous procedure to Example 651, part c, N*7*-(2,2-Difluoro-ethyl)-6,7,8,9-tetrahydro-5H-benzocycloheptene-2,7-diamine was combined with (2,5-Dichloro-pyrimidin-4-yl)-[2-(1-methyl-1H-imidazol-2-yl)-phenyl]-amine to yield 5-Chloro-N*2*-[7-(2,2-difluoro-ethylamino)-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl]-N*4*-[2-(1-methyl-1H-imidazol-2-yl)-phenyl]-pyrimidine-2,4-diamine (31.64 mg, 29% yield) as a beige foam. 1H-NMR (CDCl3) δ 10.68 (s, 1 h), 8.58 (d, J=8.68 Hz, 1H), 8.01 (s, 1H), 7.35 (m. 2H), 7.33 (s, 1H), 7.28 (m, 1H), 7.23 (m, 1H), 7.00 (m, 2H), 6.90 (s, 1H), 5.85 (m, 1H), 3.76 (s, 3H), 3.02 (t, J=9.4 Hz, 2H), 2.80 (m, 3H), 2.69 (m, 2H), 2.05 (m, 2H), 1.30 (m, 2H). LC/MS (ESI+)=523 (M+H).

Sources & evidence

ORD record
ord-4050d35f3c43431982ed2acecb585c88
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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