HCID 57522618, compound → Hydrochloric Acid
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]2[C@@H:14]3[CH2:15][C@@H:11]([CH:12]=[CH:13]3)[C@@H:10]2[C:16]([NH2:18])=[O:17])[C:5]([Cl:19])=[CH:4][N:3]=1.[NH2:20][C:21]1[CH:22]=[CH:23][C:24]2[CH2:30][CH2:29][C@H:28]([NH:31][C:32](=[O:34])[CH3:33])[CH2:27][C:26](=[O:35])[C:25]=2[C:36]=1[O:37][CH3:38]>>[ClH:1].[C:32]([NH:31][C@@H:28]1[CH2:27][C:26](=[O:35])[C:25]2[C:36]([O:37][CH3:38])=[C:21]([NH:20][C:2]3[N:7]=[C:6]([NH:8][C@@H:9]4[C@@H:14]5[CH2:15][C@@H:11]([CH:12]=[CH:13]5)[C@@H:10]4[C:16]([NH2:18])=[O:17])[C:5]([Cl:19])=[CH:4][N:3]=3)[CH:22]=[CH:23][C:24]=2[CH2:30][CH2:29]1)(=[O:34])[CH3:33]Participants
Reactant 2
Product 2
Procedure
(1S,2S,3R,4R)-3-(2,5-Dichloro-pyrimidin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide was reacted with N-((S)-2-Amino-1-methoxy-9-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-acetamide; hydrochloride, in a similar manner as Example 601b, to yield desired product (1S,2S,3R,4R)-3-[2-((S)-7-Acetylamino-1-methoxy-9-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamino)-5-chloro-pyrimidin-4-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide as a lyophylate (28%); 1H NMR (400 MHz, DMSO-d6) δ 9.07 (bs, 1H), 8.83 (bs, 1H), 8.16 (s, 1H), 8.09 (d, J=8.33 Hz, 1H), 8.00 (d, J=7.58 Hz, 1H), 7.93 (s, 1H), 7.38 (s, 1H), 7.08 (d, J=8.34 Hz, 1H), 6.36 (bs, 1H), 6.26 (bs, 1H), 3.98-3.94 (m, 2H), 3.69 (s, 3H), 2.93-2.68 (m, 7H), 2.1-1.9 (m, 2H), 1.80 (s, 3H), 1.75-1.70 (m, 1H), 1.42 (d, J=9.10 Hz, 1H); MS (m/e) 525.15 (M+H).
Sources & evidence
- ORD record
- ord-60abbc84d6d54582b9b32fb6d4b5dbe2
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552186B2
Reaction notes
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