Cyclopropylamine → 2-(2,5-Dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid cyclopropylamide

HRID 1986199Notes

Reaction equation

HRID 1986199 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[C:16]([C:17]([OH:19])=O)[C:10]=3[CH:9]=2)[C:5]([Cl:20])=[CH:4][N:3]=1.[CH:21]1([NH2:24])[CH2:23][CH2:22]1.C(N(CC)C(C)C)(C)C.Cl.C(N(CC)CCCN=C=NCC)C.ON1C2C=CC=CC=2N=N1>ClCCl.O>[CH:21]1([NH:24][C:17]([C:16]2[C:10]3[CH:9]=[C:8]([C:6]4[C:5]([Cl:20])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=4)[S:12][C:11]=3[CH:13]=[CH:14][CH:15]=2)=[O:19])[CH2:23][CH2:22]1

Participants

8

Reactant 5

HCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 99645121-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochlorideHCID 866253522-(2,5-Dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid

Product 1

HCID 866253512-(2,5-Dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid cyclopropylamideYield 99.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 2-(2,5-dichloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid (5.00 g, 15.4 mmol) in dichloromethane (100 mL) is treated at room temperature with cyclopropylamine (1.20 mL, 17.3 mmol) in the presence of N,N-diisopropylethylamine (3.00 mL, 17.2 mmol), 1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.34 g, 17.4 mmol), and 1-hydroxybenzotriazole (2.33 g, 17.2 mmol) for 20 hours. Water (20 mL) is then added, and after stirring for 20 minutes, the mixture is filtered, and dried. The obtained solid is suspended in dichloromethane (50 mL), stirred for 2 hours, filtered, and dried to provide the title compound (5.60 g, 99%).

Workup

  1. filtrationthe mixture is filtered
  2. customdried
  3. stirringstirred for 2 hours
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-0eede7e330424204b4c5dca46362b336
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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