Isovaleryl chloride → HCID 25006719, compound

HRID 1443925Notes

Reaction equation

HRID 1443925 reaction equation
[CH:1]1[C:13]([NH2:14])=[CH:12][C:11]2[CH2:15][CH2:16][CH2:17][N:9]3[C:10]=2[C:2]=1[C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:8]=13.[C:18](Cl)(=[O:23])[CH2:19][CH:20]([CH3:22])[CH3:21]>ClC(Cl)C>[CH:1]1[C:13]([NH:14][C:18](=[O:23])[CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:12][C:11]2[CH2:15][CH2:16][CH2:17][N:9]3[C:10]=2[C:2]=1[C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:8]=13

Participants

4

Reactant 2

HCID 66054Isovaleryl chlorideHCID 59168390HCID 59168390, compound

Product 1

HCID 25006719HCID 25006719, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Following the procedure of Example 1, Step 4, 5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-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-5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-2-yl-3-methylbutanamide (68 mg). MS m/z 311; HPLC purity 100% at 210-370 nm, 10.5 min.; 99.4% 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]+), 311.2122.

Sources & evidence

ORD record
ord-4e7e2b233add46c99bc97f06cf9335fb
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

Loading…