Sodium Bicarbonate → HCID 178465842, compound

HRID 2064621Notes

Reaction equation

HRID 2064621 reaction equation
[CH2:1]([O:3][C:4]1[C:29]([CH2:30][CH3:31])=[CH:28][C:7]2[NH:8][C:9]([C:11]3[C:15]([NH:16][C:17]([CH:19]4[CH2:21][CH2:20]4)=[O:18])=[CH:14][N:13](C4CCCCO4)[N:12]=3)=[N:10][C:6]=2[CH:5]=1)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]1[C:29]([CH2:30][CH3:31])=[CH:28][C:7]2[NH:8][C:9]([C:11]3[C:15]([NH:16][C:17]([CH:19]4[CH2:20][CH2:21]4)=[O:18])=[CH:14][NH:13][N:12]=3)=[N:10][C:6]=2[CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 135750746cyclopropanecarboxylic acid [3-(5-ethoxy-6-ethyl-1H-benzoimidazol-2-yl)-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]amide

Product 1

HCID 178465842HCID 178465842, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of cyclopropanecarboxylic acid [3-(5-ethoxy-6-ethyl-1H-benzoimidazol-2-yl)-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]amide [0.3 g, Reference Example 48(a)] and p-toluenesulfonic acid hydrate (1.2 g) in ethanol (25 mL) was heated in an 80° C. in an oil bath for 1 hour, then cooled, and then poured into aqueous sodium bicarbonate solution. The aqueous mixture was extracted twice with ethyl acetate (75 mL). The combined extracts were evaporated and the residue was redissolved in a mixture of methylene chloride (100 mL) and methanol (10 mL). This solution was washed with aqueous sodium bicarbonate, to remove some residual p-toluenesulfonic acid, then evaporated to give cyclopropanecarboxylic acid[3-(5-ethoxy-6-ethyl-1H-benzoimidazol-2-yl)-1H-pyrazol-4-yl]amide (120 mg) as a white solid. LC-MS (Method E): RT=2.36 minutes, 340 (M+H)+.

Workup

  1. temperaturecooled
  2. extractionThe aqueous mixture was extracted twice with ethyl acetate (75 mL)
  3. customThe combined extracts were evaporated
  4. dissolutionthe residue was redissolved in a mixture of methylene chloride (100 mL) and methanol (10 mL)
  5. washThis solution was washed with aqueous sodium bicarbonate
  6. customto remove some residual p-toluenesulfonic acid
  7. customevaporated

Sources & evidence

ORD record
ord-12c53753f7d044549b490e3b1fdbfd88
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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