D-Camphorsulfonic Acid → Chloro-N*4*-[2-(1-methyl-1H-imidazol-2-yl)-phenyl]-N*2*-[7-(2,2,2-trifluoro-ethylamino)-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl]-pyrimidine-2,4-diamine

HRID 1040985Notes

Reaction equation

HRID 1040985 reaction equation
[F:1][C:2]([F:18])([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.CC1(C)[C@]2(CS(O)(=O)=O)C(C[C@H]1CC2)=O.Cl[C:35]1[N:40]=[C:39]([NH:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[C:48]2[N:49]([CH3:53])[CH:50]=[CH:51][N:52]=2)[C:38]([Cl:54])=[CH:37][N:36]=1>>[Cl:54][C:38]1[C:39]([NH:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[C:48]2[N:49]([CH3:53])[CH:50]=[CH:51][N:52]=2)=[N:40][C:35]([NH:16][C:13]2[CH:14]=[CH:15][C:8]3[CH2:7][CH2:6][CH:5]([NH:4][CH2:3][C:2]([F:17])([F:18])[F:1])[CH2:11][CH2:10][C:9]=3[CH:12]=2)=[N:36][CH:37]=1

Participants

4

Reactant 3

HCID 65617D-Camphorsulfonic AcidHCID 86633891(2,5-Dichloro-pyrimidin-4-yl)-[2-(1-methyl-1H-imidazol-2-yl)-phenyl]-amineHCID 131729561N*7*-(2,2,2-trifluoro-ethyl)-6,7,8,9-tetrahydro-5H-benzocycloheptene-2,7-diamine

Product 1

HCID 131729563Chloro-N*4*-[2-(1-methyl-1H-imidazol-2-yl)-phenyl]-N*2*-[7-(2,2,2-trifluoro-ethylamino)-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl]-pyrimidine-2,4-diamineYield 47%

Procedure

In an analogous procedure to Example 651, part c, N*7*-(2,2,2-Trifluoro-ethyl)-6,7,8,9-tetrahydro-5H-benzocycloheptene-2,7-diamine (75 mg, 0.290 mmol) was combined with DL-10-camphorsulfonic acid (101 mg, 0.436 mmol) and (2,5-Dichloro-pyrimidin-4-yl)-[2-(1-methyl-1H-imidazol-2-yl)-phenyl]-amine (93 mg, 0.290 mmol) to yield -Chloro-N*4*-[2-(1-methyl-1H-imidazol-2-yl)-phenyl]-N*2*-[7-(2,2,2-trifluoro-ethylamino)-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl]-pyrimidine-2,4-diamine (52.73 mg, 47% yield) as a white powder. 1H-NMR (CDCl3) δ 10.71 (s, 1H), 8.56 (d, J=8.7 Hz, 1H), 8.01 (s, 1H), 7.41 (m, 2H), 7.39 (s, 1H), 7.23 (m, 1H), 7.18 (m, 1H), 7.02 (m, 3H), 3.76 (s, 3H), 3.24 (q, J=9.4, 18.8 Hz, 2H), 2.82 (m, 3H), 2.68 (m, 2H), 2.05 (m, 2H), 1.31 (m, 2H), MP=154-156° C.

Sources & evidence

ORD record
ord-d15bbd8e190943f0bade9571067bffea
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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