Dimethylformamide → HCID 24985405, compound

HRID 544925Notes

Reaction equation

HRID 544925 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=O)[CH:9]=2)=[CH:4][CH:3]=1.[CH3:17][CH2:18]N=C=NCCCN(C)C.[CH:28]1[CH:29]=[CH:30][C:31]2N(O)N=[N:34][C:32]=2[CH:33]=1.[CH3:38]CN(C(C)C)C(C)C.[CH3:47][N:48]([CH:50]=[O:51])C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([NH:34][C:32]3[CH:33]=[C:28]([C:50](=[O:51])[NH:48][CH:47]4[CH2:18][CH2:17]4)[CH:29]=[CH:30][C:31]=3[CH3:38])=[O:16])[CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27574194'-Chloro[1,1'-biphenyl]-3-carboxylic acid

Product 1

HCID 24985405HCID 24985405, compound

Procedure

To a solution of 4′-chlorobiphenyl-3-carboxylic acid (40 mg, 0.17 mmol) in DMF (0.5 mL) was added EDCI (40 mg, 0.21 mmol) and HOBt (26 mg, 0.19 mmol) and the resulting solution was stirred at rt for 15 min. At this time, DIPEA (0.042 mL, 0.26 mmol) was added and the mixture was stirred at rt for ˜16 h. Crushed ice (˜2 mL volume) was added and the mixture was stirred for 2 h and the product was collected by vacuum filtration, washed with water and dried to afford 59 mg of a white solid as the title compound (Example 128). HPLC Ret. Time=3.67 min, LCMS [M+H]+ 405.19.

Workup

  1. stirringthe mixture was stirred at rt for ˜16 h
  2. stirringthe mixture was stirred for 2 h
  3. filtrationthe product was collected by vacuum filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-9d558b54e4004aec87e37cf0f1952452
Source dataset
uspto-grants-2011_05
Patent number
US07935696B2

Reaction notes

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