Dimethylformamide → HCID 66662558, compound

HRID 2275654Notes

Reaction equation

HRID 2275654 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3([C:17]4[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=4)[CH2:16][CH2:15]3)=[O:13])[CH2:8]2)=[CH:3][CH:2]=1.[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>>[CH2:24]([O:23][C:20]1[CH:19]=[CH:18][C:17]([C:14]2([C:12]([N:9]3[CH2:10][CH2:11][CH:7]([C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)[CH2:8]3)=[O:13])[CH2:16][CH2:15]2)=[CH:22][CH:21]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 66661624HCID 66661624, compound

Product 1

HCID 66662558HCID 66662558, compoundYield 43.1%

Procedure

A mixture of 4-{1-[(3-pyridin-4-ylpyrrolidin-1-yl)carbonyl]cyclopropyl}phenol (20 mg, 0.00006 mol, example 372), benzyl bromide (7.7 μL, 0.000065 mol), and potassium carbonate (18 mg, 0.00013 mol) in N,N-dimethylformamide (200 μL, 0.002 mol) was stirred at room temperature over night. The crude product was purified with prep-HPLC to afford the product (10.3 mg). LCMS: m/z 399.0 (M+H+).

Workup

  1. customThe crude product was purified with prep-HPLC

Sources & evidence

ORD record
ord-aacadd0832e64a16b2773918e95dcec1
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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