Sodium Bicarbonate → HCID 86692604, compound

HRID 1748663Notes

Reaction equation

HRID 1748663 reaction equation
[O:1]1[CH2:4][C:3](=O)[CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:20]([C:22]1([C:28]2[N:33]=[CH:32][C:31]([NH:34][C:35]([C:37]3[CH:38]=[N:39][N:40]([C:43]4[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][N:44]=4)[C:41]=3[CH3:42])=[O:36])=[CH:30][CH:29]=2)[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)#[N:21].C(=O)(O)[O-].[Na+]>ClCCl.O1CCCC1>[C:20]([C:22]1([C:28]2[N:33]=[CH:32][C:31]([NH:34][C:35]([C:37]3[CH:38]=[N:39][N:40]([C:43]4[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][N:44]=4)[C:41]=3[CH3:42])=[O:36])=[CH:30][CH:29]=2)[CH2:23][CH2:24][N:25]([CH:3]2[CH2:2][O:1][CH2:4]2)[CH2:26][CH2:27]1)#[N:21]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 150242543-Oxetanone2×HCID 86692605HCID 86692605, compound

Product 1

HCID 86692604HCID 86692604, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Oxetanone (316 mg) and sodium triacetoxyborohydride (112 mg) were added at room temperature to a solution of N-[6-(4-cyanopiperidin-4-yl)pyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (200 mg) described in Reference Example 169 in dichloromethane (20 ml) and tetrahydrofuran (20 ml), and stirred at the same temperature for eight hours. Further 3-oxetanone (316 mg) and sodium triacetoxyborohydride (112 mg) were added at room temperature and stirred at the same temperature for six hours. After completion of the reaction, a saturated aqueous solution of sodium bicarbonate was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated and the resulting residue was purified with silica gel column chromatography (chloroform/methanol) to give the titled compound (100 mg) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customthe resulting residue was purified with silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-5eee3b91bb4a4107bd094932e3ee3c8d
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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