Acetic Acid → HCID 21936993, compound

HRID 1639548Notes

Reaction equation

HRID 1639548 reaction equation
[C:1]([OH:4])(=O)[CH3:2].[C:5]1([CH:11]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:12][CH2:13][N:14]([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[C:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)=[O:16])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>ClCCl>[C:1]([N:31]1[CH2:32][CH2:33][CH:28]([N:14]([CH2:13][CH2:12][CH:11]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=2)=[O:16])[CH2:29][CH2:30]1)(=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 21936992HCID 21936992, compound

Product 1

HCID 21936993HCID 21936993, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

117 mg (175 μmol, 3.5 eq.) of P-EDC resin is preswollen in 1.5 ml of anhydrous dichloromethane. Acetic acid (7.5 mg, 125 μmol, 2.5 eq.) is added and the mixture is agitated for 10 minutes. Then N-(3,3-diphenylpropyl)-N-(4-piperidinyl)-N′-[3-(trifluoromethyl)phenyl]urea (24.3 mg, 50 μmol) is added in its turn and the mixture is agitated overnight. The resin is filtered and the filtrate is concentrated. The oil obtained is passed through a silica gel cartridge eluting with an equimolar mixture of heptane and ethyl acetate in order to obtain 16 mg (yield=62%) of a white foam after concentration.

Workup

  1. stirringthe mixture is agitated overnight
  2. filtrationThe resin is filtered
  3. concentrationthe filtrate is concentrated
  4. customThe oil obtained
  5. washeluting with an equimolar mixture of heptane and ethyl acetate in order

Sources & evidence

ORD record
ord-308661df8f044debab3924448c1a4aad
Source dataset
uspto-grants-2012_02
Patent number
US08110574B2

Reaction notes

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