Propionyl chloride → HCID 68505456, compound

HRID 1716600Notes

Reaction equation

HRID 1716600 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([N:18]3[C:22]4[CH:23]=[CH:24][C:25]([CH3:27])=[CH:26][C:21]=4[N:20]=[C:19]3[C:28]([OH:31])([CH3:30])[CH3:29])[CH2:14][CH2:13]1)[CH2:5]2.C(N(CC)C(C)C)(C)C.[C:41](Cl)(=[O:44])[CH2:42][CH3:43]>C1COCC1>[OH:31][C:28]([C:19]1[N:18]([CH:15]2[CH2:14][CH2:13][N:12]([CH2:11][CH:6]3[CH2:5][C:4]4[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:41](=[O:44])[CH2:42][CH3:43])[CH:3]=4)[CH2:7]3)[CH2:17][CH2:16]2)[C:22]2[CH:23]=[CH:24][C:25]([CH3:27])=[CH:26][C:21]=2[N:20]=1)([CH3:29])[CH3:30]

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 68511631HCID 68511631, compound

Product 1

HCID 68505456HCID 68505456, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{1-[1-(5-amino-indan-2-ylmethyl)-piperidin-4-yl]-5-methyl-1H-benzoimidazol-2-yl}-propan-2-ol (50 mg, 0.12 mmol), N,N-diisopropylethylamine (46 mg, 0.36 mmol) in THF (3 mL) was added propionyl chloride (12 mg, 0.13 mmol). After stirring overnight, the reaction mixture was quenched with silica-supported diamine-3 (119 mg, Silicycle) to scavenge the excess propionyl chloride. The mixture was filtered and concentrated in vacuo, and the residue was purified by flash chromatography to afford N-(2-{4-[2-(1-hydroxy-1-methyl-ethyl)-5-methyl-benzoimidazol-1-yl]-piperidin-1-ylmethyl}-indan-5-yl)-propionamide (54 mg, 95%) as white solid.

Workup

  1. customthe reaction mixture was quenched with silica-supported diamine-3 (119 mg, Silicycle)
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-084fcdf576b44e2a989e457c8d0384d2
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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