Sodium Bicarbonate → HCID 178465842, compound

HRID 2182373Notes

Reaction equation

HRID 2182373 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)+. (b) 3-(1,5,6,7-Tetrahydro-1,3-diaza-s-indacen-2-yl)-1H-pyrazol-4-ylamine

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-a6d7f4e222fe400e9f898070023b2484
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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