1,1'-Carbonyldiimidazole → HCID 57542305, compound

HRID 2080293Notes

Reaction equation

HRID 2080293 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[C:11]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[N:10]=1)#[N:2].[Br:28][C:29]1[N:34]=[C:33](NC)[CH:32]=[CH:31][CH:30]=1.C1N=C[N:39](C(N2C=NC=C2)=O)[CH:38]=1>CN(C=O)C>[Br:28][C:29]1[N:34]=[C:33]([CH2:38][NH:39][C:13](=[O:14])[C:12]2[CH:16]=[CH:17][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]#[N:2])=[N:10][C:11]=2[NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 134703156-bromo-N-methylpyridin-2-amineHCID 575423046-(2-Cyanophenyl)-2-(3-fluorophenethylamino)nicotinic acid

Product 1

HCID 57542305HCID 57542305, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinic acid (582 mg, 1.61 mmol) and 6-bromo-pyridin-2-yl-methylamine (300 mg, 1.61 mmol) in DMF was added CDI (261 mg, 1.61 mmol). The reaction mixture was stirred at r.t. for 2 h. The reaction mixture was purified on RP-HPLC to give N-((6-bromopyridin-2-yl)methyl)-6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamide (700 mg, 82%) LRMS (M+H+) m/z 530.1.

Workup

  1. customThe reaction mixture was purified on RP-HPLC

Sources & evidence

ORD record
ord-e46f96a606ac42bca9440b0c7c47dd85
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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