HCID 57522618, compound → (1s,2s,3r,4r)-3-{5-Chloro-2-[7-(2,2-difluoro-ethylamino)-6,7,8,9-tetrahydro-5h-benzocyclohepten-2-ylamino]-pyrimidin-4-ylamino}-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide
Reaction equation
[F:1][CH:2]([F:19])[CH2:3][NH:4][CH:5]1[CH2:11][CH2:10][C:9]2[C:12](OC)=[C:13]([NH2:16])[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1.Cl[C:21]1[N:26]=[C:25]([NH:27][C@@H:28]2[C@@H:33]3[CH2:34][C@@H:30]([CH:31]=[CH:32]3)[C@@H:29]2[C:35]([NH2:37])=[O:36])[C:24]([Cl:38])=[CH:23][N:22]=1>>[Cl:38][C:24]1[C:25]([NH:27][C@@H:28]2[C@@H:33]3[CH2:34][C@@H:30]([CH:31]=[CH:32]3)[C@@H:29]2[C:35]([NH2:37])=[O:36])=[N:26][C:21]([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:1])[F:19])[CH2:11][CH2:10][C:9]=3[CH:12]=2)=[N:22][CH:23]=1Participants
Reactant 2
Product 1
Procedure
In an analogous procedure to Example 651, part c, N*7*-(2,2-Difluoro-ethyl)-1-methoxy-6,7,8,9-tetrahydro-5H-benzocycloheptene-2,7-diamine was combined with (1S,2S,3R,4R)-3-(2,5-Dichloro-pyrimidin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide to yield (1S,2S,3R,4R)-3-{5-Chloro-2-[7-(2,2-difluoro-ethylamino)-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamino]-pyrimidin-4-ylamino}-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (28.05 mg, 29% yield) as an off white amorphous solid. 1H-NMR (CDCl3) δ 8.16 (d, J=8.2 Hz, 1H), 7.89 (s, 1H), 7.39 (s, 1H), 6.96 (m, 1H), 6.87 (d, J=8.3 Hz, 1H), 6.37 (br s, 1H), 6.32 (br s, 1H), 5.83 (m, 1H), 5.59 (br s, 1H), 5.37 (br s, 1H), 4.36 (m, 1H), 3.72 (s, 3H), 3.22 (m, 1H), 3.03 (m, 3H), 2.95 (s, 1H), 2.83 (m, 2H), 2.66 (m, 1H), 2.50 (m, 1H), 2.24 (d, J=9.4 Hz, 1H), 2.09 (m, 2H), 1.63 (d, J=9.0 Hz, 1H), 1.30 (m, 2H). LC/MS (ESI+)=553 (M+H). MP=127.5-128.5° C.
Sources & evidence
- ORD record
- ord-6e62fa7b47884ed9a00408eff524a6d5
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552186B2
Reaction notes
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