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Aniline → 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid phenylamide

HRID 1785506
Notes
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Reaction equation

HRID 1785506 reaction equation
[CH3:1][O:2][C:3]1[C:25]([O:26][CH3:27])=[CH:24][C:6]2[N:7]([C:10]3[S:11][C:12]([C:21]([OH:23])=O)=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:14]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1.C(N(CC)C(C)C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>CN(C)C=O.C(OCC)(=O)C>[C:61]1([NH:60][C:21]([C:12]2[S:11][C:10]([N:7]3[C:6]4[CH:24]=[C:25]([O:26][CH3:27])[C:3]([O:2][CH3:1])=[CH:4][C:5]=4[N:9]=[CH:8]3)=[N:14][C:13]=2[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:23])[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6115AnilineHCID 521913N,N-Diethyl-2-propanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 236536592-(5,6-Dimethoxybenzoimidazol-1-yl)-4-phenylthiazole-5-carboxylic acid

Product 1

HCID 23654472
2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid phenylamide
Yield 87.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid (30 mg, 0.075 mmol) in dimethylformamide (1 ml) was added diethylisopropylamine (15.6 μL, 0.09 mmol) and HATU (28.5 mg, 0.075 mmol). The mixture was stirred under ambient temperature for 5 min. Aniline (6.8 μL, 0.075 mmol) was added. The mixture was stirred for 1 hr. Ethyl acetate (5 ml) was added. The mixture was washed with water (2×3 ml), brine, dried with magnesium sulfate and concentrated in vacuo. The crude was purified with flash chromatography (0 to 2% methanol dichloromethane) to afford 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid phenylamide (30 mg, 86.4%) as a yellow solid. MS m/z 457 (M+1).

Workup

  1. stirringThe mixture was stirred for 1 hr
  2. washThe mixture was washed with water (2×3 ml), brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified with flash chromatography (0 to 2% methanol dichloromethane)

Sources & evidence

ORD record
ord-d3a109297a274f87aaf18a2099d36500
Source dataset
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07504513B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes