Pyridine → HCID 178449817, compound

HRID 1053623Notes

Reaction equation

HRID 1053623 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([N:9]([CH2:19][CH:20]2[CH2:23][CH2:22][CH2:21]2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=2[F:18])=[O:8])[NH:5]C=1.[C:24]([NH:31][C@:32]([C:36]([OH:38])=O)([CH3:35])[CH2:33][CH3:34])([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C1CCC([N:45]=C=NC2CCCCC2)CC1.N1C=CC=CC=1>C(OCC)(=O)C>[C:24]([NH:31][C@@:32]([CH3:35])([CH2:33][CH3:34])[C:36]([O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:9]([CH2:19][CH:20]2[CH2:21][CH2:22][CH2:23]2)[C:7]([C:4]2[NH:5][N:45]=[C:2]([Cl:1])[CH:3]=2)=[O:8])=[C:12]([F:18])[CH:13]=1)=[O:38])([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]

Participants

6

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 14284791(R)-2-((tert-Butoxycarbonyl)amino)-2-methylbutanoic acidHCID 901023224-chloro-N-(cyclobutylmethyl)-N-(2-fluoro-4-hydroxybenzyl)-1H-pyrrole-2-carboxamide

Product 1

HCID 178449817HCID 178449817, compoundYield 0%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-N-(cyclobutylmethyl)-N-(2-fluoro-4-hydroxybenzyl)-1H-pyrrole-2-carboxamide (0.040 g, 0.118 mmol) in 3 mL ethyl acetate was added Boc-iso-Valine (0.026 g, 0.118 mmol), DCC (0.037 g, 0.178 mmol) and pyridine 0.5 mL. The reaction mixture was added at r.t. for overnight. After removal of all the solvent, the residue was purified by chromatography. (0-30% methanol/DCM) (S)-4-((3-chloro-N-(cyclobutylmethyl)-1H-pyrazole-5-carboxamido)methyl)-3-fluorophenyl 2-(Boc-amino)-2-methylbutanoate was obtained (0.030 g, 0.056 mmol, 47% yield).

Workup

  1. additionThe reaction mixture was added at r.t. for overnight
  2. customAfter removal of all the solvent
  3. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-32d28061defe445d994651e37e6336f0
Source dataset
uspto-grants-2016_07
Patent number
US09394257B2

Reaction notes

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