2-(3-Carbamoylphenylamino)-2-(3,4-dimethoxyphenyl)acetic acid → 3-((R)-1-(3,4-Dimethoxyphenyl)-2-((R)-2-(5-(3,3-dimethylureido)-2-(isopropylsulfonyl)phenyl)pyrrolidin-1-yl)-2-oxoethylamino)benzamide
Reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:10][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[C:12](O)=[O:13])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[NH2:2].Cl.[CH:26]([S:29]([C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:43])[N:40]([CH3:42])[CH3:41])=[CH:34][C:33]=1[C@H:44]1[CH2:48][CH2:47][CH2:46][NH:45]1)(=[O:31])=[O:30])([CH3:28])[CH3:27]>>[CH3:24][O:23][C:17]1[CH:16]=[C:15]([C@@H:11]([NH:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:1]([NH2:2])=[O:3])[C:12]([N:45]2[CH2:46][CH2:47][CH2:48][C@@H:44]2[C:33]2[CH:34]=[C:35]([NH:38][C:39]([N:40]([CH3:42])[CH3:41])=[O:43])[CH:36]=[CH:37][C:32]=2[S:29]([CH:26]([CH3:28])[CH3:27])(=[O:31])=[O:30])=[O:13])[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]Participants
3
Reactant 2
Product 1
Procedure
Example 56 was prepared according to the general coupling condition using 1A and 31A. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.17 (d, J=6.60 Hz, 3 H) 1.42 (d, J=7.15 Hz, 3H) 1.73 (dd, J=12.64, 5.50 Hz, 1H) 1.91-2.21 (m, 2H) 2.47 (dd, J=13.19, 7.70 Hz, 1H) 2.97 (s, 6H) 3.61 (s, 3H) 3.63-3.74 (m, 1H) 3.80-3.85 (m, 3H) 3.87-3.99 (m, 1H) 4.03-4.16 (m, 1H) 5.37 (s, 1H) 5.66 (dd, J=8.25, 4.95 Hz, 1H) 6.79 (s, 1H) 6.83-6.96 (m, 3H) 7.02 (d, J=8.25 Hz, 1H) 7.17-7.28 (m, 3H) 7.39 (dd, J=8.79, 2.20 Hz, 1H) 7.72 (d, J=8.79 Hz, 1H), LC-MS 652 (M+H).
Workup
- customExample 56 was prepared
Sources & evidence
- ORD record
- ord-8deb8b8716e94fde9fac3a5e1af4c1b8
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222453B2
Reaction notes
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