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Diethyl Pyrocarbonate → 1-[(5-chloro-2-thienyl)sulfonyl-ethyl-amino]-N-[[2-methoxy-6-[4-(trifluoromethyl)phenyl]-4-pyridyl]methyl]cyclopropanecarboxamide

HRID 1479880
Notes
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Reaction equation

HRID 1479880 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([N:10]([CH2:17][CH3:18])[C:11]2([C:14]([OH:16])=O)[CH2:13][CH2:12]2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.CCOC(OC(OCC)=O)=O.[CH2:30]([O:32][C:33]1[CH:38]=[C:37]([CH2:39][NH2:40])[CH:36]=[C:35]([C:41]2[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][CH:42]=2)[N:34]=1)C>C1COCC1>[Cl:1][C:2]1[S:6][C:5]([S:7]([N:10]([CH2:17][CH3:18])[C:11]2([C:14]([NH:40][CH2:39][C:37]3[CH:36]=[C:35]([C:41]4[CH:42]=[CH:43][C:44]([C:47]([F:48])([F:49])[F:50])=[CH:45][CH:46]=4)[N:34]=[C:33]([O:32][CH3:30])[CH:38]=3)=[O:16])[CH2:12][CH2:13]2)(=[O:8])=[O:9])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3051Diethyl PyrocarbonateHCID 903841961-[(5-Chloro-2-thienyl)sulfonyl-ethyl-amino]cyclopropanecarboxylic acidHCID 90390025[2-Ethoxy-6-[4-(trifluoromethyl)phenyl]-4-pyridyl]methanamine

Product 1

HCID 903902871-[(5-chloro-2-thienyl)sulfonyl-ethyl-amino]-N-[[2-methoxy-6-[4-(trifluoromethyl)phenyl]-4-pyridyl]methyl]cyclopropanecarboxamideYield 25.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of acid 18 (281 mg, 0.90 mmol) in THF (20 mL) was added with DEPC (0.18 mL, 1.3 mol eq) and the mixture was stirred at room temperature several minutes. Then [2-ethoxy-6-[4-(trifluoromethyl)phenyl]-4-pyridyl]methanamine 27L (300 mg, 1.1 mol eq) and a catalytic amount of TEA were added, then the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, water was added to the residue that is extracted with EtOAc (3×35 mL) and washed with brine (1×40 mL). The separated organic phase was dried over Na2SO4, evaporated to dryness and the residue was purified by flash chromatography (4/6 EtOAc/Petroleum ether) to afford a white solid (130 mg) after crystallization from ethyl ether. Yield=25%. 1HNMR (DMSO, 200 MHz) δ 1.23 (m, 4H), 1.4 (m, 6H), 3.41 (m, 2H), 4.41 (m, 4H), 6.67 (s, 1H), 7.27 (d, 1H, J=3.8), 7.58 (m, 2H), 7.86 (d, 2H, J=8), 8.28 (m, 3H). [M+1] 587.80 (C25H25ClF3N3O4S2 requires 588.06).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customThe solvent was removed under reduced pressure, water
  3. additionwas added to the residue that
  4. extractionis extracted with EtOAc (3×35 mL)
  5. washwashed with brine (1×40 mL)
  6. dry with materialThe separated organic phase was dried over Na2SO4
  7. customevaporated to dryness
  8. customthe residue was purified by flash chromatography (4/6 EtOAc/Petroleum ether)

Sources & evidence

ORD record
ord-82b9993f806e4681ae59e9f2b9a444b2
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09409864B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes