Triethylamine → HCID 11329260, compound

HRID 561302Notes

Reaction equation

HRID 561302 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-06eec3ef28104eaf9d5bf72794375563
Source dataset
uspto-grants-2011_11
Patent number
US08063222B2

Reaction notes

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