Isovaleryl chloride → HCID 25006341, compound

HRID 1443904Notes

Reaction equation

HRID 1443904 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].[C:19](Cl)(=[O:24])[CH2:20][CH:21]([CH3:23])[CH3:22]>ClC(Cl)C>[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:19](=[O:24])[CH2:20][CH:21]([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 66054Isovaleryl chlorideHCID 44248849HCID 44248849, compound

Product 1

HCID 25006341HCID 25006341, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

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 (0.10 g, 0.42 mmol), isovaleryl chloride (0.051 mL, 0.42 mmol) and poly-(4-vinylpyridine) (600 mg) in dichloroethane (15 mL) provided 0.09 g of N-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-yl-3-methylbutanamide. MS (ES) m/z 325.2; HPLC purity 100% at 210-370 nm, 10.8 min.; 99.4% at 252 nm, 10.8 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 C21H28N2O+H+, 325.22744; found (ESI, [M+H]+), 325.2269.

Sources & evidence

ORD record
ord-745f6d0315da425cb79259fe7d936d63
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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