1,1'-Carbonyldiimidazole → (2S,4S)-N-(hex-5-enyl)-1-(1H-imidazole-1-carbonyl)-4-(7-methoxy-8-methyl-2-(4-(trifluoromethyl)thiazol-2-yl)quinolin-4-yloxy)-N-methylpyrrolidine-2-carboxamide

HRID 1675448Notes

Reaction equation

HRID 1675448 reaction equation
[CH2:1]([N:7]([CH3:38])[C:8]([C@@H:10]1[CH2:14][C@H:13]([O:15][C:16]2[C:25]3[C:20](=[C:21]([CH3:28])[C:22]([O:26][CH3:27])=[CH:23][CH:24]=3)[N:19]=[C:18]([C:29]3[S:30][CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[N:33]=3)[CH:17]=2)[CH2:12][NH:11]1)=[O:9])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[C:39](N1C=CN=C1)([N:41]1[CH:45]=[CH:44][N:43]=[CH:42]1)=[O:40]>ClCCl>[CH2:1]([N:7]([CH3:38])[C:8]([C@@H:10]1[CH2:14][C@H:13]([O:15][C:16]2[C:25]3[C:20](=[C:21]([CH3:28])[C:22]([O:26][CH3:27])=[CH:23][CH:24]=3)[N:19]=[C:18]([C:29]3[S:30][CH:31]=[C:32]([C:34]([F:35])([F:36])[F:37])[N:33]=3)[CH:17]=2)[CH2:12][N:11]1[C:39]([N:41]1[CH:45]=[CH:44][N:43]=[CH:42]1)=[O:40])=[O:9])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 57816661(2S,4S)-N-(hex-5-enyl)-4-(7-methoxy-8-methyl-2-(4-(trifluoromethyl)thiazol-2-yl)quinolin-4-yloxy)-N-methylpyrrolidine-2-carboxamide

Product 1

HCID 57816712(2S,4S)-N-(hex-5-enyl)-1-(1H-imidazole-1-carbonyl)-4-(7-methoxy-8-methyl-2-(4-(trifluoromethyl)thiazol-2-yl)quinolin-4-yloxy)-N-methylpyrrolidine-2-carboxamideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Compound 127 (18.35 g) was dissolved in anhydrous dichloromethane (37 mL) under argon. 1,1′-Carbonyldiimidazole (2 eq.) was added at room temperature. The reaction mixture was stirred for 40 min. The mixture was diluted with DCM, washed with water, dried over Na2SO4, and concentrated under vacuum. Compound 128 (19.39 g) was recovered as a pale yellow foam in 99% yield over two steps and in 98% purity (HPLC).

Workup

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customCompound 128 (19.39 g) was recovered as a pale yellow foam in 99% yield over two steps and in 98% purity (HPLC)

Sources & evidence

ORD record
ord-f5178dcffb104ae19e49591dd1e6447b
Source dataset
uspto-grants-2011_08
Patent number
US08003659B2

Reaction notes

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