Triethylamine → HCID 10097552, compound

HRID 561338Notes

Reaction equation

HRID 561338 reaction equation
Cl.[CH3:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[NH:9][C:10]([C:12]1[C:21]2[C:16](=[C:17]([S:22](=[O:31])(=[O:30])[NH:23][CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)=[O:11].C(N(CC)CC)C.Cl[C:40]([O:42][CH2:43][CH3:44])=[O:41]>ClCCl>[CH2:43]([O:42][C:40]([N:27]1[CH2:26][CH2:25][CH:24]([NH:23][S:22]([C:17]2[C:16]3[C:21](=[C:12]([C:10](=[O:11])[NH:9][CH:4]4[CH2:5][CH2:6][CH2:7][CH2:8][CH:3]4[CH3:2])[CH:13]=[CH:14][CH:15]=3)[CH:20]=[CH:19][CH:18]=2)(=[O:31])=[O:30])[CH2:29][CH2:28]1)=[O:41])[CH3:44]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 66997773HCID 66997773, compound

Product 1

HCID 10097552HCID 10097552, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(Piperidin-4-ylsulfamoyl)-naphthalene-1-carboxylic acid (2-methyl-cyclohexyl)-amide hydrochloride 48 (190 mg, 0.41 mmol) was dissolved in dichloromethane (1 mL). Triethylamine (0.13 g, 0.18 mL, 1.28 mmol) was added followed by ethyl chloroformate (65 mg, 0.068 mL, 0.60 mmol). The reaction was stirred overnight at room temperature. The crude reaction mixture was charged to a flash column. Elution with 99:1 dichloromethane:methanol afforded H-24 (66 mg, 59%) as a white solid. 1H NMR (300 MHz, CDCl3) (1:1 mixture of diastereomers) δ 8.65 (d, 1H), 8.48 (d, 1H), 8.25 (d, 1H), 7.55 (m, 3H), 6.20 (d, 1H), 5.47 (m, 1H), 5.26 (s, 1H), 4.00 (m, 2H), 3.75 (m, 3H), 3.20 (m, 1H), 2.75 (m, 2H), 2.15 (m, 1H), 1.78 (m 3H), 1.57 (m 2H), 1.38 (m, 2H), 1.05 (m, 10H); LC/MS m/z 502 (M+H)+.

Workup

  1. customThe crude reaction mixture
  2. additionwas charged to a flash column
  3. washElution with 99:1 dichloromethane

Sources & evidence

ORD record
ord-83d772fb179f4f69b0cd71895d1249a8
Source dataset
uspto-grants-2011_11
Patent number
US08063222B2

Reaction notes

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