Dimethylformamide → HCID 53238432, compound

HRID 469567Notes

Reaction equation

HRID 469567 reaction equation
[C:1]1([C:7]2([CH2:10][C:11]([OH:13])=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[NH2:25][N:26]1[N:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]1=[O:40]>ClCCl>[O:40]=[C:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:34]([C:36]([F:37])([F:39])[F:38])=[N:35][N:26]1[NH:25][C:11](=[O:13])[CH2:10][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 136403147350-58-5HCID 671611112-amino-4-(trifluoromethyl)phthalazin-1(2H)-one

Product 1

HCID 53238432HCID 53238432, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(1-phenylcyclopropyl)acetic acid (0.063 g, 0.36 mmol) and oxalyl dichloride (0.042 mL, 0.48 mmol) in dichloromethane (1 mL) with a catalytic amount of DMF was stirred for 90 minutes, and concentrated. The material was re-dissolved in dichloromethane (1 mL) and the product from Example 11B (0.080 g, 0.35 mmol) was added, stirred for 2 hours, and concentrated. The residue was chromatographed on SiO2 (0-2% diethyl ether/dichloromethane) to give the title compound (52 mg) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 11.56 (s, 1H), 8.41-8.45 (m, 1H), 8.10-8.16 (m, 1H), 7.97-8.07 (m, 2H), 7.32-7.40 (m, 2H), 7.23-7.29 (m, 2H), 7.13-7.20 (m, 1H), 2.74 (s, 2H), 1.04-1.10 (m, 2H), 0.84-0.89 (m, 2H); MS (ESI−) M/Z 386 (M−H)−.

Workup

  1. concentrationconcentrated
  2. dissolutionThe material was re-dissolved in dichloromethane (1 mL)
  3. concentrationconcentrated
  4. customThe residue was chromatographed on SiO2 (0-2% diethyl ether/dichloromethane)

Sources & evidence

ORD record
ord-f72df337a8624bfaa160e90866a74088
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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