1-Hydroxybenzotriazole → HCID 25004706, compound

HRID 72682Notes

Reaction equation

HRID 72682 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:28]3[CH2:33][CH2:32][CH:31]([C:34]([OH:36])=O)[CH2:30][CH2:29]3)=[N:10][C:11]([C:24]([F:27])([F:26])[F:25])=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.[OH:49][N:50]1C2C=CC=CC=2N=N1.[CH:59](N(C(C)C)CC)(C)C>ClCCl>[CH3:59][O:49][NH:50][C:34]([CH:31]1[CH2:32][CH2:33][N:28]([C:9]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[C:13]([C:14]3[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=3)[N:12]=[C:11]([C:24]([F:25])([F:27])[F:26])[N:10]=2)[CH2:29][CH2:30]1)=[O:36]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67272171HCID 67272171, compound

Product 1

HCID 25004706HCID 25004706, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-{5-(4-fluorophenyl)-6-[4-(methylsulfonyl)phenyl]-2-(trifluoromethyl)pyrimidin-4-yl}piperidine-4-carboxylic acid (0.15 g, 0.30 mmol) in dichloromethane (5 ml) was treated with o-methyl hydroxylamine hydrochloride (0.028 g, 0.30 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.127 g, 0.663 mmol), 1-hydroxybenzotriazole (0.008 g, 0.066 mmol) and diisopropylethylamine (0.042 g, 0.33 mmol). After 2 hours of stirring the reaction mixture was poured onto ice-cold water, extracted with dichloromethane and washed with brine. Evaporation of the organic layer furnished the required compound. 1H-NMR (DMSO-d6) δ: 1.46 (m, 4H), 2.14 (m, 1H), 2.73-2.78 (m, 2H), 3.18 (s, 3H), 3.53 (s, 3H), 3.81-3.84 (m, 2H), 7.24 (d, 2H), 7.31-7.36 (m, 5H), 7.75 (d, 2H), 11.01 (br.s, 1H, D2O exchangeable); MS m/z: 535.1 (M++1).

Workup

  1. additionwas poured onto ice-cold water
  2. extractionextracted with dichloromethane
  3. washwashed with brine
  4. customEvaporation of the organic layer

Sources & evidence

ORD record
ord-6c618876622e46fab4449c7acd3dabff
Source dataset
uspto-grants-2014_09
Patent number
US08828999B2

Reaction notes

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