Triethylamine → HCID 11329260, compound

HRID 2054863Notes

Reaction equation

HRID 2054863 reaction equation
Cl.[CH:2]1([NH:8][C:9]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([S:21](=[O:30])(=[O:29])[NH:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:13][CH:12]=2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(N(CC)CC)C.Cl[C:39]([O:41][CH2:42][CH3:43])=[O:40]>ClCCl>[CH2:42]([O:41][C:39]([N:26]1[CH2:25][CH2:24][CH:23]([NH:22][S:21]([C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:11]([C:9](=[O:10])[NH:8][CH:2]3[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]3)=[CH:12][CH:13]=2)(=[O:30])=[O:29])[CH2:28][CH2:27]1)=[O:40])[CH3:43]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 16105791HCID 16105791, compound

Product 1

HCID 11329260HCID 11329260, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(Piperidin-4-ylsulfamoyl)-naphthalene-1-carboxylic acid cyclohexylamide hydrochloride F-2 (87 mg, 0.19 mmol) was dissolved and stirred in dichloromethane (2 mL). Triethylamine (58 mg, 0.08 mL, 0.57 mmol) was added followed by ethyl chloroformate (41 mg, 0.037 mL, 0.39 mmol). The reaction was stirred overnight at room temperature, then charged directly to a flash column. Elution with 99:1 dichloromethane:methanol afforded the titled compound the title compound as a white solid. Wt.: 60 mg (65%). 1H NMR (300 MHz, CDCl3) δ 8.59 (m, 1H), 8.28 (m, 1H), 8.19 (d, 1H), 7.64 (m, 2H), 7.54 (d, 1H), 4.10 (m, 1H), 4.03 (q, 2H), 3.80 (m, 2H), 3.64 (m, 1H), 3.18 (m, 1H), 2.68 (m, 2H), 2.12 (m, 2H), 1.79 (m, 2H), 1.68 (m, 1H), 1.58 (m, 2H), 1.47 (m, 2H), 1.24 (m, 6H), 1.18 (t, 3H); LC/MS m/z 488 (M+H)+.

Workup

  1. additioncharged directly to a flash column
  2. washElution with 99:1 dichloromethane

Sources & evidence

ORD record
ord-9227c28348704ddb86c786e87ac7c51e
Source dataset
uspto-grants-2008_02
Patent number
US07329755B2

Reaction notes

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