Chloride → HCID 69138517, compound

HRID 1357229Notes

Reaction equation

HRID 1357229 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[C:18]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13]([CH2:25][NH3+:26])=[CH:14]2.[Cl-].[C:28]1([N:34]2[C:38]([CH2:39][CH2:40][CH3:41])=[C:37]([C:42](Cl)=[O:43])[CH:36]=[N:35]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[CH3:24][O:23][C:21](=[O:22])[CH2:20][O:19][C:18]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:25][NH:26][C:42]([C:37]3[CH:36]=[N:35][N:34]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:38]=3[CH2:39][CH2:40][CH3:41])=[O:43])[CH:14]=2)[C:9]=1[Br:8]

Participants

6

Reactant 4

HCID 312ChlorideHCID 8471TriethylamineHCID 37757171-Phenyl-5-propyl-1H-pyrazole-4-carbonyl chlorideHCID 18505313HCID 18505313, compound

Product 1

HCID 69138517HCID 69138517, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.192 mL, 1.38 mmol) was added under nitrogen to a mixture of 5-bromo-6-methoxycarbonylmethoxy-naphthalen-2-ylmethyl-ammonium; chloride (0.25 g, 0.69 mmol), prepared in the previous step, and 1-phenyl-5-propyl-1H-pyrazole-4-carbonyl chloride (0.17 g, 0.69 mmol) in 20 mL of methylene chloride at room temperature. The reaction stirred under nitrogen for 17 h. The reaction was diluted with methylene chloride, extracted two times with water, two times with 5% sodium bicarbonate, dried (MgSO4) and the solvent removed under reduced pressure to give (1-Bromo-6-{[(1-phenyl-5-propyl-1H-pyrazole-4-carbonyl)-amino]-methyl}-naphthalen-2-yloxy)-acetic acid methyl ester (0.347 g, 95%) as a white solid, mp 144-146° C.

Workup

  1. extractionextracted two times with water, two times with 5% sodium bicarbonate
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b8dc005596b644aaa94d224b79ab2339
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

Loading…