Chloroform → HCID 69585372, compound

HRID 1828210Notes

Reaction equation

HRID 1828210 reaction equation
[C:1]([O:5][C:6](=[O:35])[CH2:7][N:8]1[C:12]([NH2:13])=[C:11]([C:14]2[CH:27]=[CH:26][C:17]3[N:18]([CH2:24][CH3:25])[C:19](=[O:23])[N:20]([CH2:21][CH3:22])[C:16]=3[CH:15]=2)[C:10]([C:28]2[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=2)=[N:9]1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(Cl)Cl>FC(F)(F)C(O)=O>[C:1]([O:5][C:6](=[O:35])[CH2:7][N:8]1[C:12]([NH2:13])=[C:11]([C:14]2[CH:27]=[CH:26][C:17]3[N:18]([CH2:24][CH3:25])[C:19](=[O:23])[N:20]([CH2:21][CH3:22])[C:16]=3[CH:15]=2)[C:10]([C:28]2[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=2)=[N:9]1)([CH3:2])([CH3:3])[CH3:4].[CH2:24]([N:18]1[C:17]2[CH:26]=[CH:27][C:14]([C:11]3[C:10]([C:28]4[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=4)=[N:9][N:8]4[CH2:7][C:6](=[O:35])[NH:13][C:12]=34)=[CH:15][C:16]=2[N:20]([CH2:21][CH3:22])[C:19]1=[O:23])[CH3:25]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 69585372HCID 69585372, compound

Product 2

HCID 69585372HCID 69585372, compoundHCID 135724447HCID 135724447, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

[5-Amino-4-(1,3-diethyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-3-m-tolyl-pyrazol-1-yl]-acetic acid tert-butyl ester is prepared according to Example 338. [5-Amino-4-(1,3-diethyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-3-m-tolyl-pyrazol-1-yl]-acetic acid tert-butyl ester (0.06 g) is diluted with 50% trifluoroacetic acid is chloroform and stirred for 5 hours. The reaction is concentrated then treated sequentially with chloroform (2 mL) 1-hydroxybenzotriazole hydrate (0.026 g), diisopropylethylamine (0.06 mL) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.036 g). The mixture is allowed to stir for 20 hours, is diluted with saturated sodium bicarbonate and extracted with ethyl acetate. After concentration the product is purified on silica gel to give 1,3-Diethyl-5-(2-oxo-6-m-tolyl-2,3-dihydro-1H-imidazo[1,2-b]pyrazol-7-yl)-1,3-dihydro-benzoimidazol-2-one.

Workup

  1. concentrationThe reaction is concentrated
  2. additionthen treated sequentially with chloroform (2 mL) 1-hydroxybenzotriazole hydrate (0.026 g), diisopropylethylamine (0.06 mL) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.036 g)
  3. stirringto stir for 20 hours
  4. additionis diluted with saturated sodium bicarbonate
  5. extractionextracted with ethyl acetate
  6. concentrationAfter concentration the product
  7. customis purified on silica gel

Sources & evidence

ORD record
ord-7a33fb2c041347acbad1810681ab1cd5
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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