Carbamic acid, (3-cyanopropyl)-, 1,1-dimethylethyl ester (9CI) → tert-Butyl 2-(5-((S)-2-amino-3-(1H-indol-3-yl)propylamino)-3-(isoquinolin-6-yl)isoxazol-4-yl)ethylcarbamate
Reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][NH:6][C:7](=O)OC(C)(C)C)#[N:2].[C:14]([O:18][C:19]([NH:21][CH2:22][CH2:23][C:24]1[C:25]([C:36]2[CH:37]=[C:38]3[C:43](=[CH:44][CH:45]=2)[CH:42]=[N:41][CH:40]=[CH:39]3)=[N:26][O:27][C:28]=1[NH:29][C:30](=O)OCC=C)=[O:20])([CH3:17])([CH3:16])[CH3:15].C1C2[C:50](=[CH:51][C:52](C3C=C(NC(=O)OCC=C)ON=3)=CC=2)[CH:49]=[CH:48]N=1>>[NH2:2][C@@H:1]([CH2:3][C:4]1[C:52]2[C:7](=[CH:48][CH:49]=[CH:50][CH:51]=2)[NH:6][CH:5]=1)[CH2:30][NH:29][C:28]1[O:27][N:26]=[C:25]([C:36]2[CH:37]=[C:38]3[C:43](=[CH:44][CH:45]=2)[CH:42]=[N:41][CH:40]=[CH:39]3)[C:24]=1[CH2:23][CH2:22][NH:21][C:19](=[O:20])[O:18][C:14]([CH3:17])([CH3:15])[CH3:16]Participants
4
Reactant 3
Product 1
Procedure
This compound was synthesized in an analogous manner to Example 32 but using tert-butyl 3-cyanopropylcarbamate instead of acetonitrile in the preparation of 2-propen-1-yl (4-(2-((tert-butoxycarbonyl)amino)ethyl)-3-(6-isoquinolinyl)-5-isoxazolyl)carbamate according to Scheme 6 instead of allyl 3-(isoquinolin-6-yl)isoxazol-5-ylcarbamate. MS m/z: 527 (M+1); 1H NMR (400 MHz, CD3OD) δ ppm 9.75 (s, 1H), 8.63 (d, J=6.26 Hz, 1H), 8.51-8.57 (m, 3H), 8.20 (d, J=8.61 Hz, 1H), 7.61 (d, J=8.02 Hz, 1H), 7.40 (d, J=8.22 Hz, 1H), 7.26-7.29 (m, 1H), 7.15 (t, J=7.53 Hz, 1H), 7.08 (t, J=7.43 Hz, 1H), 3.73-3.86 (m, 3H), 3.13-3.24 (m, 4H), 2.62 (t, J=6.94 Hz, 2H), 1.33 (s, 9H).
Workup
- customThis compound was synthesized in an analogous manner to Example 32
Sources & evidence
- ORD record
- ord-af5f8e45cd28477ba4da964d81c6bb53
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897619B2
Reaction notes
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