Water → (S)-7-(1-cyanopiperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetra hydropyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 64381Notes

Reaction equation

HRID 64381 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:28]([C:29]([NH2:31])=[O:30])=[C:17]3[NH:18][CH2:19][CH2:20][C@@H:21]([CH:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)[N:16]3[N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].O.Br[C:39]#[N:40]>C(Cl)Cl.[Cl-].[Na+].O>[C:39]([N:25]1[CH2:24][CH2:23][CH:22]([C@H:21]2[N:16]3[N:15]=[C:14]([C:11]4[CH:10]=[CH:9][C:8]([O:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)=[CH:13][CH:12]=4)[C:28]([C:29]([NH2:31])=[O:30])=[C:17]3[NH:18][CH2:19][CH2:20]2)[CH2:27][CH2:26]1)#[N:40]

Participants

7

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 136928097Pyrazolo[1,5-a]pyrimidine-3-carboxamide, 4,5,6,7-tetrahydro-2-(4-phenoxyphenyl)-7-(4-piperidinyl)-, (7S)-

Product 1

HCID 136928114(S)-7-(1-cyanopiperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetra hydropyrazolo[1,5-a]pyrimidine-3-carboxamideYield 75%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (S)-2-(4-phenoxyphenyl)-7-(piperidin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide (417 mg, 1 mmol) in DCM (20 mL) was added NaHCO3 (168 mg, 2 mmol) and water (5 mL), followed by BrCN (127 mg, 1.2 mmol). The mixture was stirred at RT for 16 h. To the mixture was added DCM (50 mL) and brine (20 mL). The organic phase was further washed with brine (100 mL), dried over Na2SO4. Concentrated and purified by Pre-TLC (DCM/MeOH, 50/1) to afford 330 mg (75%) of white solid. MS (ESI) m/e [M+1]+ 443.0.

Workup

  1. washThe organic phase was further washed with brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationConcentrated
  4. custompurified by Pre-TLC (DCM/MeOH, 50/1)

Sources & evidence

ORD record
ord-cca8e7d3fd0241838e349bde05873a71
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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