N-methyl-2-pyrrolidone → HCID 86621912, compound

HRID 1400099Notes

Reaction equation

HRID 1400099 reaction equation
[C:1]([NH:3][C:4](=[N:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][N:22]([CH:25]3[CH2:30][CH:29]4[CH2:31][CH:26]3[CH2:27][CH2:28]4)[CH2:21][CH2:20]2)=[CH:15][CH:14]=1)[O:5][C:6]1C=CC=CC=1)#[N:2].[Cl:32][C:33]1[N:34]=[C:35]([NH:43][NH2:44])[C:36]2[S:41][CH:40]=[C:39]([CH3:42])[C:37]=2[N:38]=1.CN1C(=[O:51])CCC1>>[CH:6]([OH:5])=[O:51].[C@@H:26]12[CH2:31][C@@H:29]([CH2:28][CH2:27]1)[CH2:30][C@@H:25]2[N:22]1[CH2:23][CH2:24][N:19]([C:16]2[CH:17]=[CH:18][C:13]([NH:12][C:4]3[N:3]=[C:1]([NH2:2])[N:43]([C:35]4[C:36]5[S:41][CH:40]=[C:39]([CH3:42])[C:37]=5[N:38]=[C:33]([Cl:32])[N:34]=4)[N:44]=3)=[CH:14][CH:15]=2)[CH2:20][CH2:21]1

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 59774522HCID 59774522, compoundHCID 72558186HCID 72558186, compound

Product 1

HCID 86621912HCID 86621912, compoundYield 31%

Conditions

Temperature
180 °C

Procedure

A mixture of N-cyano-N′-{4-[4-(bicyclo[2.2.1]hept-2-yl)-1-piperazinyl]phenyl}-O-phenylisourea (50 mg; 0.12 mmol; 1.0 equiv) and 2-chloro-4-hydrazino-7-methylthieno[3,2-d]pyrimidine (26 mg; 0.12 mmol; 1 equiv) in 0.5 mL of NMP was heated in the microwave apparatus at 180° C. for 6 min. Purification by HPLC gave N3-(4-(4-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-yl)piperazin-1-yl)phenyl)-1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-1H-1,2,4-triazole-3,5-diamine formic acid, compound #139, as a yellow solid (20 mg; 31% yield); 1H-NMR (DMSO-d6, 300 MHz) 9.20 (br. s, 1H), 8.21 (s, 1H), 7.90 (br. s, 2H), 7.56 (d, J=8.7 Hz, 2H), 6.92 (d, J=8.7 Hs, 2H), 3.10-3.02 (m, 4H), 2.45-2.40 (m, 4H), 2.30-2.15 (m, 3H), 1.78-1.62 (m, 2H), 1.50-1.40 (m, 1H), 1.37-1.14 (m, 4H), 0.90-0.86 (m, 1H) ppm; MS (ES) 536.19 (M+H), 534.26 (M−H).

Workup

  1. customPurification by HPLC

Sources & evidence

ORD record
ord-727c53d25a524babac4d50a77eacb94c
Source dataset
uspto-grants-2014_12
Patent number
US08906922B2

Reaction notes

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