3-Cyclopentylpropionyl chloride → HCID 25006716, compound

HRID 1443916Notes

Reaction equation

HRID 1443916 reaction equation
[CH:1]1[C:9]([NH2:10])=[CH:8][C:7]2[CH2:11][CH2:12][N:5]3[C:6]=2[C:2]=1[C:3]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:4]=13.[CH:18]1([CH2:23][CH2:24][C:25](Cl)=[O:26])[CH2:22][CH2:21][CH2:20][CH2:19]1>ClC(Cl)C>[CH:18]1([CH2:23][CH2:24][C:25]([NH:10][C:9]2[CH:1]=[C:2]3[C:6]4=[C:7]([CH2:11][CH2:12][N:5]4[C:4]4[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:3]3=4)[CH:8]=2)=[O:26])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 660393-Cyclopentylpropionyl chlorideHCID 59168382HCID 59168382, compound

Product 1

HCID 25006716HCID 25006716, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Following the procedure of Example 1, Step 4, 4,5,8,9,10,11-hexahydro-7H-cyclohepta[b]pyrrolo[3,2,1-hi]indole-2-amine (0.10 g, 0.44 mmol), 3-cyclopentylpropionyl chloride (0.068 mL, 0.44 mmol) and poly-(4-vinylpyridine) (600 mg) in dichloroethane (15 mL) provided 3-cyclopentyl-N-4,5,8,9,10,11-hexahydro-7H-cyclohepta[b]pyrrolo[3,2,1-hi]indol-2-ylpropanamide (10 mg). MS (ESI) m/z 351; HPLC purity 100% at 210-370 nm, 11.4 min.; 100% at 250 nm, 11.4 min. (Xterra RP18, 3.5 u, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN and MeOH) for 10 min, hold 4 min); HRMS: calcd for C23H30N2O+H+, 351.24309; found (ESI, [M+H]+), 351.2423.

Sources & evidence

ORD record
ord-c8b21fa5ddf44ac0adef5c2fd09a3b76
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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