1-Hydroxybenzotriazole → N-[3-(2,3-dimethyl-3H-imidazol-4-yl)-phenyl]-[2,2']bithiophenyl-5-carboxamide

HRID 1835470

Reaction equation

HRID 1835470 reaction equation
[S:1]1[C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=[C:2]1[C:9]1[S:10][CH:11]=[CH:12][CH:13]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH3:36][N:37]1[C:41]([C:42]2[CH:43]=[C:44]([CH:46]=[CH:47][CH:48]=2)[NH2:45])=[CH:40][N:39]=[C:38]1[CH3:49]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:49][C:38]1[N:37]([CH3:36])[C:41]([C:42]2[CH:43]=[C:44]([NH:45][C:6]([C:5]3[S:1][C:2]([C:9]4[S:10][CH:11]=[CH:12][CH:13]=4)=[CH:3][CH:4]=3)=[O:8])[CH:46]=[CH:47][CH:48]=2)=[CH:40][N:39]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 1509652,2'-Bithiophene-5-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 235036623-(1,2-dimethyl-1H-imidazol-5-yl)aniline

Product 1

HCID 69899339N-[3-(2,3-dimethyl-3H-imidazol-4-yl)-phenyl]-[2,2']bithiophenyl-5-carboxamideYield 61.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of [2,2′]bithiophenyl-5-carboxylic acid (105 mg) and 1-hydroxybenzotriazole (81 mg) in dichloromethane (2 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (144 mg) and the mixture was stirred for 15 minutes. After adding 3-(1,2-dimethylimidazol-5-yl)aniline (94 mg) and 4-dimethylaminopyridine (92 mg), the mixture was stirred for 24 hours. The mixture was diluted with dichloromethane and washed with water and brine. The mixture was dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by a silica gel column chromatography eluting with 3% methanol in dichloromethane to give N-[3-(2,3-dimethyl-3H-imidazol-4-yl)-phenyl]-[2,2′]bithiophenyl-5-carboxamide (117 mg, 61.6%).

Workup

  1. stirringthe mixture was stirred for 24 hours
  2. washwashed with water and brine
  3. dry with materialThe mixture was dried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by a silica gel column chromatography
  6. washeluting with 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-368687d2cde84cb3af405a9b0a251b07
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Linked notes

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