Acetic Acid → HCID 21936993, compound

HRID 2267078Notes

Reaction equation

HRID 2267078 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-14903e4e45a8445fbbb40ac16b12108f
Source dataset
uspto-grants-2010_12
Patent number
US07858789B2

Reaction notes

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