N,N-Dimethylaminoethyl chloride hydrochloride → HCID 136983680, compound

HRID 64378Notes

Reaction equation

HRID 64378 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][N:12]3[N:14]=[C:15]([C:20]4[CH:25]=[CH:24][C:23]([O:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[CH:22][CH:21]=4)[C:16]([C:17]([NH2:19])=[O:18])=[C:11]3[NH:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl.Cl[CH2:35][CH2:36][N:37]([CH3:39])[CH3:38]>>[CH3:38][N:37]([CH3:39])[CH2:36][CH2:35][O:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][N:12]3[N:14]=[C:15]([C:20]4[CH:25]=[CH:24][C:23]([O:26][C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=5)=[CH:22][CH:21]=4)[C:16]([C:17]([NH2:19])=[O:18])=[C:11]3[NH:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 1369281086-(3-Hydroxyphenyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 136983680HCID 136983680, compound

Procedure

The desired product was prepared from 6-(3-hydroxyphenyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide and 2-chloro-N,N-dimethylethanamine hydrochloride using the procedure similar to step 7 for compound 9. 1H NMR (400 MHz, DMSO-d6) δ 7.52 (d, J=8.4 Hz, 2H), 7.46-7.38 (m, 2H), 7.29 (t, J=7.6 Hz, 1H), 7.18 (t, J=7.6 Hz, 1H), 7.10-7.05 (m, 4H), 6.98-6.96 (m, 2H), 6.90-6.88 (m, 1H), 6.81 (d, J=2.4 Hz, 1H), 4.25-4.20 (m, 1H), 4.16-4.11 (m, 3H), 3.50-3.47 (m, 1H), 3.43-3.38 (m, 2H), 2.96-2.84 (m, 2H) and 2.43 (s, 6H). MS (ESI) m/e [M+1]+ 497.9.

Sources & evidence

ORD record
ord-2d20c12c1bf04456a76f5bbe6b236cf2
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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