3,3-Dimethylbutanoyl chloride → HCID 25007101, compound

HRID 1443931Notes

Reaction equation

HRID 1443931 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]([CH2:23][C:24](Cl)=[O:25])([CH3:22])([CH3:21])[CH3:20]>ClCCl>[CH3:20][C:19]([CH3:22])([CH3:21])[CH2:23][C:24]([NH:10][C:9]1[CH:1]=[C:2]2[C:6]3=[C:7]([CH2:11][CH2:12][N:5]3[C:4]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:3]2=3)[CH:8]=1)=[O:25]

Participants

4

Reactant 2

HCID 815143,3-Dimethylbutanoyl chlorideHCID 59168388HCID 59168388, compound

Product 1

HCID 25007101HCID 25007101, compoundYield 36.7%

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), t-butylacetyl chloride (0.063 mL, 0.54 mmol) and poly-(4-vinylpyridine) (500 mg) in dichloromethane (12 mL) provided 3,3-dimethyl-N-4,5,7,8,9,10,11,12-octahydrocycloocta[b]pyrrolo[3,2,1-hi]indol-2-ylbutanamide (67 mg). MS (ES) m/z 339.2; HPLC purity 100% at 210-370 nm, 11.1 min.; 100% at 250 nm, 11.1 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]+), 339.2441.

Sources & evidence

ORD record
ord-a2fdfc43628b48caa8d15402bc76985b
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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