1-Hydrazinoisoquinoline → 1-(isoquinolin-1-yl)-N3-(2-(pyrrolidin-1-ylmethyl)benzo[d]oxazol-5-yl)-1H-1,2,4-triazole-3,5-diamine
Reaction equation
[C:1](/[N:3]=[C:4](\OC1C=CC=CC=1)/[NH:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12]([CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[N:11][C:10]=2[CH:20]=1)#[N:2].[NH:28]([C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][N:31]=1)[NH2:29]>CN1CCCC1=O>[C:30]1([N:28]2[C:1]([NH2:2])=[N:3][C:4]([NH:5][C:6]3[CH:7]=[CH:8][C:9]4[O:13][C:12]([CH2:14][N:15]5[CH2:16][CH2:17][CH2:18][CH2:19]5)=[N:11][C:10]=4[CH:20]=3)=[N:29]2)[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][N:31]=1Participants
Procedure
A solution of (Z)-phenyl N′-cyano-N-(2-(pyrrolidin-1-ylmethyl)benzo[d]oxazol-5-yl)carbamimidate (36 mg, 0.1 mmol) and 1-hydrazinoisoquinoline in N-methyl-2-pyrrolidone (0.5 mL) was shaken at 100° C. for 3 hours. After cooling to ambient temperature, the volatiles were evaporated under reduced pressure. The residue was purified by HPLC eluting with acetonitrile-water to provide 1-(isoquinolin-1-yl)-N3-(2-(pyrrolidin-1-ylmethyl)benzo[d]oxazol-5-yl)-1H-1,2,4-triazole-3,5-diamine, compound #1; 1H NMR (CD3OD, 300 MHz) 8.98 (d, J=8.4 Hz, 1H), 8.36 (d, J=5.7 Hz, 1H), 7.99 (d, J=8.1 Hz, 1H), 7.84-7.58 (m, 4H), 7.26 (dd, J=2.4, 8.7 Hz, 1H), 6.99 (d, J=9.0 Hz, 1H), 5.05 (s, 2H), 3.76 (m, 2H), 3.65 (m, 2H), 3.30 (m, 3H), 2.11 (m, 4H) ppm; MS (ES) 427.16 (M+H).
Workup
- customthe volatiles were evaporated under reduced pressure
- customThe residue was purified by HPLC
- washeluting with acetonitrile-water
Sources & evidence
- ORD record
- ord-1596a616722a4a22a257bcdb08121d81
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796259B2
Reaction notes
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