Sodium Bicarbonate → HCID 178509142, compound

HRID 2105522Notes

Reaction equation

HRID 2105522 reaction equation
[C:1]1([C:7]2[C:8]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][N:22]4[CH2:27][CH2:26][CH:25]([C:28]5[CH:32]=[C:31]([C:33]6[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=6)[NH:30][N:29]=5)[CH2:24][CH2:23]4)=[CH:17][CH:16]=3)=[N:9][CH:10]=[C:11]([CH:14]=2)[C:12]#[N:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N[NH:40][C:41]([NH2:43])=[S:42].C(=O)(O)[O-].[Na+]>C(O)(C(F)(F)F)=O>[C:1]1([C:7]2[CH:14]=[C:11]([C:12]3[S:42][C:41]([NH2:43])=[N:40][N:13]=3)[CH:10]=[N:9][C:8]=2[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:32]=[C:31]([C:33]5[CH:34]=[CH:35][N:36]=[CH:37][CH:38]=5)[NH:30][N:29]=4)[CH2:24][CH2:23]3)=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723789ThiosemicarbazideHCID 178510336HCID 178510336, compound

Product 1

HCID 178509142HCID 178509142, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5-phenyl-6-(4-{[4-(5-pyridin-4-yl-1H-pyrazol-3-yl)piperidin-1-yl]methyl}phenyl)nicotinonitrile (4B-5; 0.030 g, 0.060 mmol) and thiosemicarbazide (0.006 g, 0.066 mmol) in TFA (1.5 mL) were heated to 60° C. for 16 hr. The reaction was then cooled, poured onto ice and basified with saturated aqueous sodium bicarbonate. The resulting precipitate (4B-6) was filtered, taken up in DMF and purified by reverse phase HPLC (5% CH3CN: 95% H2O+0.1% TFA to 95% CH3—CN: 5% H2O+0.01% TFA). 1H-NMR (500 MHz, d6 DMSO) δ 13.54 (bs, 1H), 9.64 (s, 1H), 9.07 (d, J=1.96, 1H), 8.81 (d, J=6.11, 2H), 8.21 (s, 2H), 8.10 (d, J=2.2, 1H), 7.65 (s, 2H), 7.23-7.49 (m, 9H), 7.00 (s, 1H), 4.33 (d, 2H), 3.45 (d, J=10.5, 2H), 2.95-3.15 (m, 3H), 2.21 (d, J=12.69, 2H), 1.76-1.90 (m 2H). HRMS m/z (M+H) Calcd: 571.2387, found: 571.2359.

Workup

  1. temperatureThe reaction was then cooled
  2. additionpoured onto ice
  3. filtrationThe resulting precipitate (4B-6) was filtered
  4. custompurified by reverse phase HPLC (5% CH3CN: 95% H2O+0.1% TFA to 95% CH3—CN: 5% H2O+0.01% TFA)

Sources & evidence

ORD record
ord-1096339c37de40159a62a9b13b39cb2f
Source dataset
uspto-grants-2009_08
Patent number
US07579355B2

Reaction notes

Loading…