Pyridine → HCID 67160882, compound

HRID 469569Notes

Reaction equation

HRID 469569 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:16].N1C=CC=CC=1.[S:23]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](Cl)=[O:30])=[CH:24]1>ClCCl>[O:16]=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([C:12]([F:15])([F:13])[F:14])=[N:11][N:2]1[NH:1][C:29](=[O:30])[CH2:28][C:25]1[CH:26]=[CH:27][S:23][CH:24]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27606223-Thiopheneacetyl chlorideHCID 671611112-amino-4-(trifluoromethyl)phthalazin-1(2H)-one

Product 1

HCID 67160882HCID 67160882, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the product of Example 11B (30.2 mg, 0.13 mmol), pyridine (0.14 mL, 0.17 mmol), and 2-(thiophen-3-yl)acetyl chloride (24.0 mg, 0.15 mmol) in dichloromethane (0.4 mL) was stirred for 3 hours, concentrated, and chromatographed (20% acetone/hexanes) to give the title compound (33.8 mg) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 11.82-11.94 (m, 1H), 8.44 (dd, J=7.9, 1.5 Hz, 1H), 8.11-8.17 (m, 1H), 8.00-8.09 (m, 2H), 7.36-7.58 (m, 2H), 7.14 (dd, J=4.9, 1.3 Hz, 1H), 3.74 (s, 2H); MS (ESI−) M/Z 352 (M−H)−.

Workup

  1. concentrationconcentrated
  2. customchromatographed (20% acetone/hexanes)

Sources & evidence

ORD record
ord-d06c018523204c088d326ede77360cd1
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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