Diisopropylethylamine → (R)-N-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamide

HRID 85175

Reaction equation

HRID 85175 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[C:17]([C:18](O)=[O:19])[C:11]=2[N:10]=1.[CH3:23][C:24]1([CH3:38])[O:28][C@H:27]([CH2:29][O:30][C:31]2[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=2)[NH2:34])[CH2:26][O:25]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.O>[CH3:23][C:24]1([CH3:38])[O:28][C@H:27]([CH2:29][O:30][C:31]2[CH:32]=[C:33]([NH:34][C:18]([C:17]3[C:11]4[N:10]=[C:9]([C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=5[C:2]([F:1])([F:21])[F:22])[NH:13][C:12]=4[CH:14]=[CH:15][CH:16]=3)=[O:19])[CH:35]=[CH:36][CH:37]=2)[CH2:26][O:25]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58552948HCID 58552948, compoundHCID 672016022-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid

Product 1

HCID 67203479(R)-N-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2-(2-(Trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid (3; 75 mg, 0.24 mmol) was taken up in NMP (2 mL) along with (R)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)aniline (133; 64.3 mg, 0.288 mmol) and HATU (186 mg, 0.49 mmol). DIEA (81 μL, 0.49 mmol) was added and the resulting reaction mixture was stirred at room temperature for 12 h. The temperature was then raised to 60° C. and the reaction mixture was allowed to stir for an additional 1 h. The reaction mixture was diluted with water and filtered. The collected solids were further purified by silica gel chromatography to afford the desired product 134, as a yellow solid (51.5 mg, 42%).

Workup

  1. customthe resulting reaction mixture
  2. temperatureThe temperature was then raised to 60° C.
  3. stirringto stir for an additional 1 h
  4. filtrationfiltered
  5. customThe collected solids were further purified by silica gel chromatography

Sources & evidence

ORD record
ord-930a91f7a1494d79b2bed38bf4945ef7
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Linked notes

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