4-Fluoro-2-(5-hydroxymethyl-[1,2,4]triazol-1-yl)-benzonitrile → [2-(2-Aminomethyl-5-fluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-methanol hydrochloride

HRID 1372344Notes

Reaction equation

HRID 1372344 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N:10]2[C:14]([CH2:15][OH:16])=[N:13][CH:12]=[N:11]2)[CH:3]=1.[ClH:17].FC1C=CC(CN)=C(N2C=CC=N2)C=1>>[ClH:17].[NH2:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([F:1])=[CH:3][C:4]=1[N:10]1[C:14]([CH2:15][OH:16])=[N:13][CH:12]=[N:11]1

Participants

3

Reactant 2

HCID 210699014-Fluoro-2-(5-hydroxymethyl-[1,2,4]triazol-1-yl)-benzonitrileHCID 210699174-Fluoro-2-pyrazol-1-yl-benzylamine hydrochloride

Product 1

HCID 21069781[2-(2-Aminomethyl-5-fluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-methanol hydrochlorideYield 100%

Procedure

This compound was prepared from 4-fluoro-2-(5-hydroxymethyl-[1,2,4]triazol-1-yl)-benzonitrile by the hydrogenation method used for the preparation of 4-fluoro-2-pyrazol-1-yl-benzylamine hydrochloride. Yield: 100% (grayish green powder). HPLC rt=0.33 min. LC/MS m/z 223 (M+H). 1H NMR (DMSO-d6, 500 MHz) δ ppm 3.76 (2H, q, J=5.8 Hz, 7-NCH2), 4.55 (2H, s, 9-OCH2), 7.54–7.60 (1H, m, 5-CH), 7.62 (1H, dd, J=9, 2.6 Hz, 3-CH), 7.89 (1H, dd, J=8.7, 6.0 Hz, 6-CH), 8.26 (1H, s, 8-CH), 8.58 (3H, br.s, NH3). 13C NMR (DMSO-d6, 125.8 Hz) δ ppm 37.1 (7-NCH2), 54.2 (10-OCH2), 114.6 (d, J=24 Hz, 3-CH), 117.0 (d, J=21 Hz, 5-CH), 127.1 (d, J=3.8 Hz, 1-C), 132.2 (d, J=8.6 Hz, 6-CH), 136.9 (d, J=111 Hz, 2-C), 151.0 (9-CH), 156.3 (8-C), 161.3 (d, J=247 Hz, 4-CF). HRMS (ESI) calcd for C10H12FN4O (M+H) 223.0995. found 223.0988 (δ −3.2 ppm).

Workup

  1. customHPLC rt=0.33 min

Sources & evidence

ORD record
ord-f36eb9c6b7d5414db59ddd6f1148b232
Source dataset
uspto-grants-2007_01
Patent number
US07157447B2

Reaction notes

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