Sodium Carbonate → 4-((1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-1H-pyrazole-1-carboxamide

HRID 594974Notes

Reaction equation

HRID 594974 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([NH:14][C:15]3[CH:16]=[N:17][NH:18][CH:19]=3)=[N:12][CH:13]=[C:8]2[CH:7]=[N:6]1.[O-:24][C:25]#[N:26].[K+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O>[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([NH:14][C:15]3[CH:19]=[N:18][N:17]([C:25]([NH2:26])=[O:24])[CH:16]=3)=[N:12][CH:13]=[C:8]2[CH:7]=[N:6]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11378442Potassium cyanateHCID 67112034HCID 67112034, compound

Product 1

HCID 529132844-((1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-1H-pyrazole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a solution of 1-(2-fluorobenzyl)-N-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine (Example 88), (111 mg, 0.36 mmol) in ACN/H2O (9:1, 4 mL) was added potassium cyanate (35 mg, 1.2 eq). After 30 min at rt, the reaction mixture was neutralized with saturated sodium carbonate and the aqueous phase extracted with DCM. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative HPLC to give the title product. 1H NMR (d6-DMSO) δ 10.12 (s, 1H), 9.00 (s, 1H), 8.57 (s, 1H), 8.12 (s, 1H), 7.94 (s, 1H), 7.80 (s, 1H), 7.71 (s, 1H), 7.41-7.28 (m, 2H), 7.26-7.14 (m, 2H), 5.58 (s, 2H); LC-MS method B, (ES+) 353.0, RT=7.75 min.

Workup

  1. extractionthe aqueous phase extracted with DCM
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-f912df6f54814e00a83cd8188dfd8b47
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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