Sodium Bicarbonate → HCID 178515133, compound

HRID 1526131Notes

Reaction equation

HRID 1526131 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[C:25]([C:26](OCC)=[O:27])=[C:24]([C:31]4[C:36]([F:37])=[CH:35][CH:34]=[C:33]([F:38])[C:32]=4[F:39])[NH:23][C:22]4[NH:40][N:41]=[C:42]([C:43]5[S:44][CH:45]=[CH:46][CH:47]=5)[C:21]3=4)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(=O)(O)[O-].[Na+]>C1(C)C(C)=CC=CC=1>[N:11]1([C:14]2[CH:19]=[C:18]3[C:17](=[CH:16][CH:15]=2)[C:20]2=[C:21]4[C:42]([C:43]5[S:44][CH:45]=[CH:46][CH:47]=5)=[N:41][NH:40][C:22]4=[N:23][C:24]([C:31]4[C:36]([F:37])=[CH:35][CH:34]=[C:33]([F:38])[C:32]=4[F:39])=[C:25]2[C:26]3=[O:27])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 178468536HCID 178468536, compound

Product 1

HCID 178515133HCID 178515133, compoundYield 3.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

10 g of polyphosphoric acid is added to a solution of 2 g (3 mmol) of ethyl 4-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-3-(thiophen-2-yl)-6-(2,3,6-trifluorophenyl)-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate in xylene (20 ml). The reaction mixture is carried at 160° C. for 36 hours. After returning to room temperature, the reaction medium is poured over crushed ice. Saturated sodium bicarbonate solution is added until the reaction medium is neutralized and then the product is extracted with ethyl acetate. The organic phases are combined, dried on magnesium sulfate and concentrated. The residue is purified by silica gel chromatography (eluent: 88:12 dichloromethane/methanol) to yield 50 mg (3%) of 8-(piperazin-1-yl)-1-(thiophen-2-yl)-5-(2,3,6-trifluorophenyl)indeno[1,2-d]pyrazolo[3,4-b]pyridin-6(3H)-one in the form of a pinkish solid.

Workup

  1. customAfter returning to room temperature
  2. additionthe reaction medium is poured
  3. customover crushed ice
  4. extractionthe product is extracted with ethyl acetate
  5. customdried on magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel chromatography (eluent: 88:12 dichloromethane/methanol)

Sources & evidence

ORD record
ord-45fe2c3a962849e89fbeef532297ffc2
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

Loading…