Cyclopropanecarbonyl chloride → HCID 68510060, compound

HRID 1716590Notes

Reaction equation

HRID 1716590 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[CH3:28])[CH:14]([CH2:29][OH:30])[CH2:13]1)[CH2:5]2.C(N(C(C)C)CC)(C)C.[CH:40]1([C:43](Cl)=[O:44])[CH2:42][CH2:41]1>C(Cl)Cl>[CH3:28][C:19]1[N:18]([CH:15]2[CH2:16][CH2:17][N:12]([CH2:11][C@H:6]3[CH2:5][C:4]4[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:43](=[O:44])[CH:40]([CH3:42])[CH3:41])[CH:3]=4)[CH2:7]3)[CH2:13][CH:14]2[CH2:29][OH:30])[C:22]2[CH:23]=[CH:24][C:25]([CH3:27])=[CH:26][C:21]=2[N:20]=1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 68512348HCID 68512348, compound

Product 1

HCID 68510060HCID 68510060, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[1-(5-Amino-indan-2-ylmethyl)-4-(2,5-dimethyl-benzoimidazol-1-yl)-piperidin-3-yl]-methanol (65 mg; 0.165 mmol) was dissolved in CH2Cl2 (1 mL). Diisopropylethylamine (70 μL; 0.4 mmol) and cyclopropanecarbonyl chloride (18 μL; 0.2 mmol) were added and the reaction mixture was stirred for one hour. All volatiles were removed and N-{(R)-2-[4-(2,5-Dimethyl-benzoimidazol-1-yl)-3-hydroxymethyl-piperidin-1-ylmethyl]-indan-5-yl}-isobutyramide was isolated by flash chromatography (1-10% CH3OH in EtOAc) as a waxy oil (68 mg; 90%).

Workup

  1. customAll volatiles were removed

Sources & evidence

ORD record
ord-aa168092687c480a8c456316f967793f
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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