Triethylamine → HCID 68277947, compound

HRID 931534Notes

Reaction equation

HRID 931534 reaction equation
[CH:1]1([S:7]([CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=3)[O:14][C:15]=2[CH3:16])(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][NH2:33])[CH:27]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C)C=O.O>[CH:1]1([S:7]([CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([NH:33][CH2:32][C:28]4[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=4)=[O:23])=[CH:19][CH:18]=3)[O:14][C:15]=2[CH3:16])(=[O:8])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 310183-PyridinemethanamineHCID 757711-HydroxybenzotriazoleHCID 68278046HCID 68278046, compound

Product 1

HCID 68277947HCID 68277947, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(4-(cyclohexylsulfonylmethyl)-5-methyloxazol-2-yl)benzoic acid (500 mg, 1.38 mmol, 1.00 equiv), pyridin-3-ylmethanamine (180 mg, 1.67 mmol, 1.20 equiv), EDCI (320 mg, 1.68 mmol, 1.20 equiv), HOBt (220 mg, 1.63 mmol, 1.20 equiv) and triethylamine (420 mg, 4.16 mmol, 3.00 equiv) in N,N-dimethylformamide (10 mL) was stirred overnight at room temperature. The reaction mixture was diluted with 15 mL of water and ice. The precipitate was collected by filtration, washed with water and dried in a vacuum oven to give 0.25 g (40%) of 4-(4-(cyclohexylsulfonylmethyl)-5-methyloxazol-2-yl)-N-(pyridin-3-ylmethyl)benzamide as a white solid LC-MS: (ES, m/z): 454 [M+H]+, 347, 306, 238, 120 1HNMR (400 MHz, CDCl3, ppm) δ 8.97 (s, 1H), 8.57 (s, 2H), 8.21-8.05 (t, 4H), 7.54 (s, 2H), 4.73 (s, 2H), 4.17 (s, 2H), 3.02-2.98 (d, 2H), 2.90-2.50 (m, 6H), 2.31-2.20 (d, 2H), 1.95 (s, 2H), 1.74-1.61 (m, 3H), 1.29 (s, 3H

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-02e7e157382f4c56bd7aeca2fa201d85
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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