Pivaloyl chloride → HCID 25005967, compound

HRID 1443900Notes

Reaction equation

HRID 1443900 reaction equation
[CH:1]1[C:10]2[C:11]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[N:8]3[C:9]=2[C:4]([CH2:5][CH2:6][CH2:7]3)=[CH:3][C:2]=1[NH2:18].[CH3:19][C:20]([CH3:25])([CH3:24])[C:21](Cl)=[O:22]>ClCCl>[CH:1]1[C:10]2[C:11]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[N:8]3[C:9]=2[C:4]([CH2:5][CH2:6][CH2:7]3)=[CH:3][C:2]=1[NH:18][C:21](=[O:22])[C:20]([CH3:25])([CH3:24])[CH3:19]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 44248849HCID 44248849, compound

Product 1

HCID 25005967HCID 25005967, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure of Example 1, Step 4, 5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-amine (0.12 g, 0.50 mmol), trimethylacetyl chloride (0.065 mL, 0.52 mmol) and poly-(4-vinylpyridine) (700 mg) in dichloromethane (10 mL) provided 0.11 g of N-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-yl-2,2-dimethylpropanamide. MS (ESI) m/z 325; HPLC purity major: no impurities detected at 210-370 nm window; 99.5% at 246 nm (max. abs), RT=10.7 (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 C21H28N2O+H+, 325.22744; found (ESI, [M+H]+), 325.2271.

Sources & evidence

ORD record
ord-205a7cc3d3794116a096fe17cd7f2467
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

Loading…