Isovaleryl chloride → HCID 25006715, compound

HRID 1443915Notes

Reaction equation

HRID 1443915 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.[C:18](Cl)(=[O:23])[CH2:19][CH:20]([CH3:22])[CH3:21]>ClC(Cl)C>[CH:1]1[C:9]([NH:10][C:18](=[O:23])[CH2:19][CH:20]([CH3:22])[CH3:21])=[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

Participants

4

Reactant 2

HCID 66054Isovaleryl chlorideHCID 59168382HCID 59168382, compound

Product 1

HCID 25006715HCID 25006715, compoundYield 19.8%

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), isovaleryl chloride (0.054 mL, 0.44 mmol) and poly-(4-vinylpyridine) (600 mg) in dichloroethane (15 mL) provided N-4,5,8,9,10,11-hexahydro-7H-cyclohepta[b]pyrrolo[3,2,1-hi]indol-2-yl-3-methylbutanamide (27 mg). MS (ESI) m/z 311; HPLC purity 98.5% at 210-370 nm, 10.5 min.; 99.5% at 250 nm, 10.5 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 C20H26N2O+H+, 311.21179; found (ESI, [M+H]+), 311.2120.

Sources & evidence

ORD record
ord-c3bf6ad7ee064bd2ae0a24cff884cc1c
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

Loading…