Tetrahydrofuran → HCID 11295662, compound

HRID 2111786Notes

Reaction equation

HRID 2111786 reaction equation
[F:1][C:2]([F:31])([F:30])[O:3][C:4]1[CH:29]=[CH:28][C:7]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:25]([OH:27])=O)=[CH:24][C:19]=4[N:18]=[CH:17]3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.C1N=CN([C:37]([N:39]2[CH:43]=[N:42][CH:41]=[CH:40]2)=O)C=1.C1[CH2:48][O:47][CH2:46]C1>>[N:39]1([CH2:40][CH2:41][NH:42][C:25]([C:23]2[CH:22]=[CH:21][C:20]3[N:16]([C:13]4[CH:12]=[CH:11][C:10]([O:9][CH2:8][C:7]5[CH:6]=[CH:5][C:4]([O:3][C:2]([F:31])([F:1])[F:30])=[CH:29][CH:28]=5)=[CH:15][CH:14]=4)[CH:17]=[N:18][C:19]=3[CH:24]=2)=[O:27])[CH2:37][CH2:48][O:47][CH2:46][CH2:43]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 69064692HCID 69064692, compound

Product 1

HCID 11295662HCID 11295662, compound

Procedure

A 0.3 M THF solution of 1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxylic acid (100 mg, 0.23 mmol) and CDI (76 mg, 0.46 mmol) was stirred at 60° C. for 4 h, after which the mixture was treated with a primary or secondary amine (0.35 mmol) and heating continued for a further 16 h. After this time, the mixture was concentrated in vacuo and the resulting residue purified by chromatography over silica gel. Recrystallization of the eluted product afforded

Workup

  1. temperatureheating
  2. concentrationAfter this time, the mixture was concentrated in vacuo
  3. customthe resulting residue purified by chromatography over silica gel
  4. customRecrystallization of the eluted product
  5. customafforded

Sources & evidence

ORD record
ord-0956bff1cac4479a87cbe0adcc396f95
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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