Oxalyl chloride → HCID 58691603, compound

HRID 856012Notes

Reaction equation

HRID 856012 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]3[CH:15]=[C:14]([C:16]4[CH:17]=[C:18]([C:21]([OH:23])=O)[S:19][CH:20]=4)[CH:13]=[N:12][C:11]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:27])=O>ClCCl>[C:1]1([C:7]2[CH:8]=[N:9][N:10]3[CH:15]=[C:14]([C:16]4[CH:17]=[C:18]([C:21]([Cl:27])=[O:23])[S:19][CH:20]=4)[CH:13]=[N:12][C:11]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 58691599HCID 58691599, compound

Product 1

HCID 58691603HCID 58691603, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)thiophene-2-carboxylic acid (5-3, 1.0 g, 3.11 mmol, 1 equiv) and oxalyl chloride (2.17 mL, 24.9 mmol, 8.00 equiv) in dichloromethane (400 mL) was stirred at 23° C. for 72 hours. The reaction mixture was concentrated to give 4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)thiophene-2-carbonyl chloride (5-4) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.89 (d, 1H, J=2.4 Hz), 8.79 (d, 1H, J=2.2 Hz), 8.50 (s, 1H), 8.22 (d, 1H, J=1.6 Hz), 8.05 (br d, 2H, J=7.8 Hz), 8.00 (d, 1H, J=1.6 Hz), 7.48 (br t, 2H, J=7.7 Hz), 7.31 (t, 1H, J=7.5 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-c94ccc1401a345d097035125528b394f
Source dataset
uspto-grants-2007_08
Patent number
US07262199B2

Reaction notes

Loading…