2-Thiophenecarbonyl chloride → HCID 25006340, compound

HRID 1443903Notes

Reaction equation

HRID 1443903 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].[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](Cl)=[O:25]>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:24]([C:20]1[S:19][CH:23]=[CH:22][CH:21]=1)=[O:25]

Participants

4

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 44248849HCID 44248849, compound

Product 1

HCID 25006340HCID 25006340, compoundYield 57.1%

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), 2-thiophenecarbonyl chloride (0.056 mL, 0.52 mmol) and poly-(4-vinylpyridine) (700 mg) in dichloromethane (10 mL) provided 0.10 g of N-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-ylthiophene-2-carboxamide. MS (ESI) m/z 351; HPLC purity major: no impurities detected at 210-370 nm window; 98.7% at 240 nm (max. abs), RT=10.9 (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 C21H22N2OS+H+, 351.15256; found (ESI, [M+H]+), 351.1516.

Sources & evidence

ORD record
ord-117fa5366d7446d69a81f9ab9adaa339
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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