Sodium Bicarbonate → HCID 11365019, compound

HRID 2105520Notes

Reaction equation

HRID 2105520 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:11]3[CH2:16][CH2:15][N:14]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([C:24]5[C:31]([C:32]6[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=6)=[CH:30][C:27]([C:28]#[N:29])=[CH:26][N:25]=5)=[CH:20][CH:19]=4)[CH2:13][CH2:12]3)[N:9]=[CH:10][C:3]=12.N[NH:39][C:40]([NH2:42])=[S:41].C(=O)(O)[O-].[Na+]>C(O)(C(F)(F)F)=O>[NH2:42][C:40]1[S:41][C:28]([C:27]2[CH:30]=[C:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:24]([C:21]3[CH:20]=[CH:19][C:18]([CH2:17][N:14]4[CH2:15][CH2:16][CH:11]([N:8]5[C:4]6=[N:5][CH:6]=[N:7][C:2]([NH2:1])=[C:3]6[CH:10]=[N:9]5)[CH2:12][CH2:13]4)=[CH:23][CH:22]=3)=[N:25][CH:26]=2)=[N:29][N:39]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723789ThiosemicarbazideHCID 11306301HCID 11306301, compound

Product 1

HCID 11365019HCID 11365019, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 6-(4-{[4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl]methyl}phenyl)-5-phenylnicotinonitrile (4A-4; 0.035 g, 0.072 mmol) and thiosemicarbazide (0.010 g, 0.108 mmol) in TFA (2 mL) was 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 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+0.1% TFA). 1H-NMR (500 MHz, d6 DMSO) δ 9.72 (bs, 1H), 9.07 (d, J=2.19, 1H), 8.93 (bs, 1H), 8.42 (bs, 1H), 8.36 (s, 1H), 8.29 (s, 1H), 8.10 (d, J=1.96, 1H), 7.65 (bs, 2H), 7.22-7.49 (m, 9H), 4.93-5.03 (m, 1H), 4.34 (s, 2H), 3.49 (d, J=12.21, 2H), 3.19-3.35 (m, 2H), 2.32-2.56 (m, 2H), 2.15 (d, J=11.96, 2H). HRMS m/z (M+H) Calcd: 561.2292, found: 561.2256.

Workup

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

Sources & evidence

ORD record
ord-b1432e8f95364e46ae336fece4eeb644
Source dataset
uspto-grants-2009_08
Patent number
US07579355B2

Reaction notes

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