Valeryl chloride → HCID 25006713, compound

HRID 1443913Notes

Reaction equation

HRID 1443913 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][CH2:20][CH2:21][CH3:22]>ClCCl>[CH:1]1[C:9]([NH:10][C:18](=[O:23])[CH2:19][CH2:20][CH2:21][CH3:22])=[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 61186Valeryl chlorideHCID 59168382HCID 59168382, compound

Product 1

HCID 25006713HCID 25006713, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 (0.13 g, 0.57 mmol), valeryl chloride (0.068 mL, 0.57 mmol) and poly-(4-vinylpyridine) (600 mg) in dichloromethane (15 mL) provided N-4,5,8,9,10,11-hexahydro-7H-cyclohepta[b]pyrrolo[3,2,1-hi]indol-2-ylpentanamide (35 mg). MS (ESI) m/z 311; HPLC purity 100% at 210-370 nm, 10.6 min.; 100% at 250 nm, 10.6 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]+), 311.2118.

Sources & evidence

ORD record
ord-5a4da92d85524752a6b43a1821f27d38
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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