Triethylamine → HCID 68278673, compound

HRID 931475Notes

Reaction equation

HRID 931475 reaction equation
C(N(CC)CC)C.[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH2:15])[CH:9]=1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([S:29]([CH2:32][C:33]2[N:34]=[C:35]([C:39]3[CH:47]=[CH:46][C:42]([C:43](O)=[O:44])=[CH:41][CH:40]=3)[O:36][C:37]=2[CH3:38])(=[O:31])=[O:30])[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH:15][C:43]([C:42]2[CH:41]=[CH:40][C:39]([C:35]3[O:36][C:37]([CH3:38])=[C:33]([CH2:32][S:29]([CH:26]4[CH2:27][CH2:28][N:23]([C:21]([O:20][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:22])[CH2:24][CH2:25]4)(=[O:30])=[O:31])[N:34]=3)=[CH:47][CH:46]=2)=[O:44])[CH:9]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 310183-PyridinemethanamineHCID 757711-HydroxybenzotriazoleHCID 68277962HCID 68277962, compound

Product 1

HCID 68278673HCID 68278673, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (440 mg, 4.36 mmol, 3.00 equiv) was added dropwise with stirring to a solution of pyridin-3-ylmethanamine (170 mg, 1.57 mmol, 1.10 equiv), 4-(4-((1-(tert-butoxycarbonyl)piperidin-4-ylsulfonyl)methyl)-5-methyloxazol-2-yl)benzoic acid (670 mg, 1.44 mmol, 1.00 equiv), EDCI (330 mg, 1.73 mmol, 1.20 equiv) and HOBT (230 mg, 1.70 mmol, 1.20 equiv) in N,N-dimethylformamide (10 mL) contained in a 50-mL round-bottom flask. The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 30 mL of water/ice. The precipitate was collected by filtration and dried in an oven under reduced pressure to give 0.74 g (93%) of tert-butyl 4-((2-(4-((pyridin-3-ylmethyl)carbamoyl)phenyl)-5-methyloxazol-4-yl)methylsulfonyl)piperidine-1-carboxylate as a yellow solid. LC-MS: (ES, m/z): 555 [M+H]+, 455.

Workup

  1. customcontained in a 50-mL round-bottom flask
  2. customThe reaction was then quenched by the addition of 30 mL of water/ice
  3. filtrationThe precipitate was collected by filtration
  4. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-94350e9453ff49ab8d8f6b03830a0321
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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