Triethylamine → HCID 178479478, compound

HRID 278619Notes

Reaction equation

HRID 278619 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([S:17]([C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[C:25]([Cl:30])[CH:26]=4)[CH:21]=3)(=[O:19])=[O:18])[CH2:13][CH2:12]2)=[O:10])[CH2:5][CH2:4]1.Cl.[C:32](N1C=CC=N1)(=[NH:34])[NH2:33].C(N(CC)CC)C>CO>[ClH:30].[Cl:30][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([S:17]([N:14]1[CH2:13][CH2:12][N:11]([C:9]([C@H:6]3[CH2:7][CH2:8][C@@H:3]([NH:2][C:32]([NH2:34])=[NH:33])[CH2:4][CH2:5]3)=[O:10])[CH2:16][CH2:15]1)(=[O:18])=[O:19])[CH:29]=[CH:28]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 178479259HCID 178479259, compound

Product 1

HCID 178479478HCID 178479478, compoundYield 161.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(cis-4-aminocyclohexane-1-ylcarbonyl)-4-(6-chloronaphthalene-2-sulfonyl)piperazine hydrochloride (100 mg), 1-amidinopyrazole hydrochloride (47 mg) and triethylamine (100 mg) in methanol (10 ml)was stirred at room temperature for 1 day. The reaction solution was concentrated, and to the residue was added dichloromethane. The mixture was washed with 1 N sodium hydroxide aqueous solution, dried and concentrated. The residue was dissolved in ethyl acetate and transformed into hydrochloride with hydrochloric acid to give a colorless solid of the title compound (88 mg).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionto the residue was added dichloromethane
  3. washThe mixture was washed with 1 N sodium hydroxide aqueous solution
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in ethyl acetate

Sources & evidence

ORD record
ord-f6f93ecdfa094f739106c0124900b067
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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