Water → HCID 18387455, compound

HRID 2296746Notes

Reaction equation

HRID 2296746 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][N:17]([CH3:40])[CH2:18][CH2:19][CH:20]1[CH:26]=[CH:25][N:24]([C:27](=[O:35])[C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)[C:23]2[CH:36]=[CH:37][CH:38]=[CH:39][C:22]=2[S:21]1.C(N(CC)CC)C.O>C(Cl)Cl>[CH3:40][N:17]([CH3:16])[CH2:18][CH2:19][CH:20]1[CH:26]=[CH:25][N:24]([C:27](=[O:35])[C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:9](=[O:10])[C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:30][CH:29]=2)[C:23]2[CH:36]=[CH:37][CH:38]=[CH:39][C:22]=2[S:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12563768[1,1'-Biphenyl]-2-carbonyl chlorideHCID 18387443HCID 18387443, compound

Product 1

HCID 18387455HCID 18387455, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Phenylbenzoyl chloride (0.36 g, 1.67 mM)(prepared from 2-biphenylcarboxylic acid as described in Example 3) was slowly added to a solution of Compound 12 as prepared in Example 7 (0.5 g, 1.4 mM) and triethylamine (0.38 ml, 3.3 mM)in methylene chloride (30 ml). The mixture was stirred at room temperature for 16 hours and water (80 ml) was added. The layers were separated. The methylene chloride layer was dried (MgSO4), filtered and evaporated in vacuo to give a crude product. Purification by flash column chromatography (EM silica gel 60; 30% EtOAc in CH2Cl2) yielded the desired product as a white solid. m/z (MH+) 536.

Workup

  1. customThe layers were separated
  2. dry with materialThe methylene chloride layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto give a crude product
  6. customPurification by flash column chromatography (EM silica gel 60; 30% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-e13d0e13c2654d669c8b926babf644d2
Source dataset
uspto-grants-2002_12
Patent number
US06489321B1

Reaction notes

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