Cyclopropylamine → HCID 86625353, compound

HRID 1986204Notes

Reaction equation

HRID 1986204 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]3[C:13]([O:20][CH3:21])=[CH:14][CH:15]=[C:16]([C:17]([OH:19])=O)[C:10]=3[CH:9]=2)[C:5]([Cl:22])=[CH:4][N:3]=1.C([N:26]([CH:29]([CH3:31])[CH3:30])CC)(C)C.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C1(N)CC1>ClCCl>[CH:29]1([NH:26][C:17]([C:16]2[C:10]3[CH:9]=[C:8]([C:6]4[C:5]([Cl:22])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=4)[S:12][C:11]=3[C:13]([O:20][CH3:21])=[CH:14][CH:15]=2)=[O:19])[CH2:31][CH2:30]1

Participants

7

Reactant 5

HCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86625354HCID 86625354, compound

Product 1

HCID 86625353HCID 86625353, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 2-(2,5-dichloropyrimidin-4-yl)-7-methoxybenzo[b]thiophene-4-carboxylic acid (2.50 g, 3.07 mmol) is added diisopropylethylamine (1.12 mL, 6.44 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (617 mg, 3.22 mmol) and 1-hydroxybenzotriazole (435 mg, 3.22 mmol) at room temperature under nitrogen atmosphere. The mixture is treated with cyclopropylamine (184 mg, 3.22 mmol) and stirred at room temperature for 1 day. The mixture is diluted with dichloromethane (60 mL) and washed with water (3×30 mL). The organic phase suspension is filtered off to give a yellow solid which is washed with dichloromethane and water to give the title compound as a yellow solid (880 mg, 72% yield).

Workup

  1. washwashed with water (3×30 mL)
  2. filtrationThe organic phase suspension is filtered off
  3. customto give a yellow solid which
  4. washis washed with dichloromethane and water

Sources & evidence

ORD record
ord-c1903f2f6f3443da957e5b1a1ce89bdc
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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