Hexanoyl chloride → HCID 25007100, compound

HRID 1443930Notes

Reaction equation

HRID 1443930 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[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:4]=13.[C:19](Cl)(=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>ClCCl>[CH:1]1[C:9]([NH:10][C:19](=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:8][C:7]2[CH2:11][CH2:12][N:5]3[C:6]=2[C:2]=1[C:3]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:4]=13

Participants

4

Reactant 2

HCID 67340Hexanoyl chlorideHCID 59168388HCID 59168388, compound

Product 1

HCID 25007100HCID 25007100, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure of Example 1, Step 4, 4,5,7,8,9,10,11,12-octahydrocycloocta[b]pyrrolo[3,2,1-hi]indol-2-amine (0.15 g, 0.54 mmol), hexanoyl chloride (0.075 mL, 0.54 mmol) and poly-(4-vinylpyridine) (500 mg) in dichloromethane (12 mL) provided N-4,5,7,8,9,10,11,12-octahydrocycloocta[b]pyrrolo[3,2,1-hi]indol-2-ylhexanamide (66 mg). MS (ES) m/z 339.2; HPLC purity 100% at 210-370 nm, 11.2 min.; 100% at 250 nm, 11.2 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 C22H30N2O+H+, 339.24309; found (ESI, [M+H]+), 339.2433.

Sources & evidence

ORD record
ord-f404eb99074742e2a9c6f468a674ea7b
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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