2-Mercaptoethanol → N-((S)-2-amino-3-(1H-indol-3-yl)propyl)-3-(isoquinolin-6-yl)isoxazol-5-amine
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH:29]S(C2C=CC([N+]([O-])=O)=CC=2)(=O)=O)[CH2:12][NH:13][C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[CH:25]=[N:24][CH:23]=[CH:22]4)[CH:15]=2)=[CH:2]1.N1CCCN2CCCCCC=12.SCCO>CN(C=O)C>[NH2:29][C@@H:11]([CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)[CH2:12][NH:13][C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[CH:25]=[N:24][CH:23]=[CH:22]3)[CH:15]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To 25 mL of round-bottom flask was added N-((S)-3-(1H-indol-3-yl)-1-(3-(isoquinolin-6-yl)isoxazol-5-ylamino)propan-2-yl)-4-nitrobenzenesulfonamide (75 mg, 132 μmol), 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (20 mg, 132 μmol) (commercially available from Aldrich), 2-mercaptoethanol (10 mg, 132 μmol) and 2 mL of DMF. After 2 hours, the reaction mixture was directly purified by preparative LC to give N-((S)-2-amino-3-(1H-indol-3-yl)propyl)-3-(isoquinolin-6-yl)isoxazol-5-amine (38 mg, 75% yield). MS m/z: 384 (M+1); 1H NMR (400 MHz, CD3OD) δ ppm 9.69 (s, 1H), 8.61 (d, J=6.26 Hz, 1H), 8.48 (d, J=8.61 Hz, 1H), 8.37-8.42 (m, 2H), 8.18 (dd, J=8.71, 1.27 Hz, 1H), 7.63 (d, J=7.82 Hz, 1H), 7.46 (d, J=8.22 Hz, 1H), 7.29 (s, 1H), 7.20 (t, J=7.53 Hz, 1H), 7.08 (t, J=7.43 Hz, 1H), 3.81-3.83 (m, 1H), 3.60-3.63 (m, 1H), 3.46-3.54 (m, 1H), 3.20 (d, J=7.24 Hz, 2H),
Workup
- customthe reaction mixture was directly purified by preparative LC
Sources & evidence
- ORD record
- ord-bc99565d51764deb9f22ef97101ad43d
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897619B2
Reaction notes
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