Sodium Hydroxide → HCID 67061071, compound

HRID 1623909Notes

Reaction equation

HRID 1623909 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[CH:21]3[CH2:22][CH:20]3[CH2:19][C:8]=2[N:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])[N:10]=1)=[O:5])C.COC(C1C2C3CC3CC=2N(C2C=CC(F)=CC=2F)N=1)=O.[OH-].[Na+]>CO.C1COCC1>[F:18][C:12]1[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=1[N:9]1[C:8]2[CH2:19][CH:20]3[CH2:22][CH:21]3[C:7]=2[C:6]([C:4]([OH:5])=[O:3])=[N:10]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 67061067HCID 67061067, compoundHCID 67061081HCID 67061081, compound

Product 1

HCID 67061071HCID 67061071, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 1-(2,4-difluoro-phenyl)-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazole-3-carboxylic acid ethyl ester (0.66 g, 2.169 mmol) and 1-(2,4-difluoro-phenyl)-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazole-3-carboxylic acid methyl ester (0.08 g, 0.276 mmol) in methanol (6 mL) and THF (6.00 mL) was added a 2.0 M aqueous solution of sodium hydroxide (3.25 mL, 6.51 mmol). The resulting yellow solution was stirred at 20° C. for 16 h. The organic solvents were removed under reduced pressure. The remaining aqueous solution was diluted with water (25 mL) then acidified to pH 2 by addition of 6 M HCl. The resulting precipitate was collected by filtration, rinsed with water, and then dried under reduced pressure to give the title compound as a tan solid (0.575 g). LCMS m/z=277.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.28 (td, J=4.4, 3.8 Hz, 1H), 1.12 (td, J=7.6, 4.7 Hz, 1H), 2.10-2.15 (m, 1H), 2.19-2.23 (m, 1H), 2.79 (d, J=17.0 Hz, 1H), 2.98 (dd, J=17.0, 6.6 Hz, 1H), 7.25-7.29 (m, 1H), 7.56-7.60 (m, 1H), 7.72 (td, J=8.8, 6.2 Hz, 1H), 12.83 (s, 1H).

Workup

  1. customThe organic solvents were removed under reduced pressure
  2. additionThe remaining aqueous solution was diluted with water (25 mL)
  3. additionthen acidified to pH 2 by addition of 6 M HCl
  4. filtrationThe resulting precipitate was collected by filtration
  5. washrinsed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-9b35ca97628d46418cc5da1e17f1d2d5
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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