Ammonium Acetate → HCID 178468536, compound

HRID 1526129Notes

Reaction equation

HRID 1526129 reaction equation
O=[C:2]([C:9]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]([F:16])[C:10]=1[F:17])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:18]([C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]2)=[CH:22][CH:21]=1)=O.[S:39]1[CH:43]=[CH:42][CH:41]=[C:40]1[C:44]1[CH:48]=[C:47]([NH2:49])[NH:46][N:45]=1.C([O-])(=O)C.[NH4+]>O.C(OCC)(=O)C>[C:35]([O:34][C:32]([N:29]1[CH2:30][CH2:31][N:26]([C:23]2[CH:24]=[CH:25][C:20]([CH:18]3[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([C:9]4[C:14]([F:15])=[CH:13][CH:12]=[C:11]([F:16])[C:10]=4[F:17])[NH:49][C:47]4[NH:46][N:45]=[C:44]([C:40]5[S:39][CH:43]=[CH:42][CH:41]=5)[C:48]3=4)=[CH:21][CH:22]=2)[CH2:27][CH2:28]1)=[O:33])([CH3:38])([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 517165Ammonium AcetateHCID 2795509Tert-butyl 4-(4-formylphenyl)piperazine-1-carboxylateHCID 13550004HCID 13550004, compoundHCID 178507300HCID 178507300, compound

Product 1

HCID 178468536HCID 178468536, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

250 mg (1.02 mmol) of ethyl 3-oxo-3-(2,3,6-trifluorophenyl)propanoate, 295 mg (1.02 mmol) of tert-butyl 4-(4-formylphenyl)piperazine-1-carboxylate, 168 mg (1.02 mmol) of 3-(thiophen-2-yl)-1H-pyrazol-5-amine and 196 mg (2.54 mmol) of ammonium acetate are added to a test tube which is then sealed. The mixture is carried without solvent at 120° C. for 1 hour. After returning to room temperature, the solid is dissolved in a water/ethyl acetate mixture. The phases are separated and the aqueous phase is extracted several times with ethyl acetate. The organic phases are combined, dried on magnesium sulfate and concentrated. The residue is purified by silica gel chromatography (eluent: 6:4 cyclohexane/ethyl acetate) to yield 300 mg (44%) 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 the form of a light yellow powder.

Workup

  1. customis then sealed
  2. customAfter returning to room temperature
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted several times with ethyl acetate
  5. customdried on magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel chromatography (eluent: 6:4 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-f40a1b85b19848b6992462f2928adac8
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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