1-Hydroxybenzotriazole → HCID 69524345, compound

HRID 858153Notes

Reaction equation

HRID 858153 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][CH:5]([S:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)[CH2:6]2.[C:18]([C:21]1[N:22]=[CH:23][S:24][CH:25]=1)(O)=[O:19].ON1C2C=CC=CC=2N=N1.N=C=N>CN(C=O)C>[CH3:1][N:2]1[CH:3]2[CH2:9][CH2:8][CH:7]1[CH2:6][CH:5]([S:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:18]([C:21]3[N:22]=[CH:23][S:24][CH:25]=3)=[O:19])=[CH:15][CH:16]=1)[CH2:4]2

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 3042714-Thiazolecarboxylic acidHCID 58762858HCID 58762858, compound

Product 1

HCID 69524345HCID 69524345, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[(8-methyl-8-azabicylo[3.2.1]oct-3-yl)thio]phenylamine (50 mg), 4-carboxythiazole (52 mg), 1-hydroxybenzotriazole (61 mg) and carbodiimide resin (1.7 mmol/g, 470 mg) in DMF (7 ml) was stirred at room temperature for 3 days. The mixture was filtered then passed through an SCX cartridge, eluting with methanol followed by 2M ammonia in methanol, providing N-{4-[(8-methyl-8-azabicylo[3.2.1]oct-3-yl)thio]phenyl]-4-thiazolecarboxamide as a white solid (55 mg)

Workup

  1. filtrationThe mixture was filtered
  2. washeluting with methanol

Sources & evidence

ORD record
ord-6d3f1811d41246ee8927386e83dbaee6
Source dataset
uspto-grants-2006_12
Patent number
US07148236B2

Reaction notes

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