Hydrochloric Acid → HCID 52914753, compound

HRID 594966Notes

Reaction equation

HRID 594966 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]3[N:14]([CH2:17][C:18]4[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=4[C:20]([O:22]C)=[O:21])[N:15]=[CH:16][C:11]3=[CH:10][N:9]=2)[CH:4]=[N:3]1.[OH-].[Na+].Cl>C1COCC1>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]3[N:14]([CH2:17][C:18]4[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=4[C:20]([OH:22])=[O:21])[N:15]=[CH:16][C:11]3=[CH:10][N:9]=2)[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67112223HCID 67112223, compound

Product 1

HCID 52914753HCID 52914753, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-((6-(1-methyl-1H-pyrazol-4-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)benzoate (15 mg, 0.04 mmol) and sodium hydroxide (1 mL, 4M aqueous solution) in THF (3 mL) was stirred at rt for 2 h. The mixture was then acidified with HCl (2M) and extracted into EtOAc. The organic phase was collected, dried (MgSO4) and concentrated in vacuo to give the title product. 1H NMR (d6-DMSO) δ 9.86 (s, 1H), 8.94 (s, 1H), 8.11 (s, 1H), 7.93 (d, 1H), 7.89 (s, 1H), 7.47 (s, 1H), 7.36-7.41 (m, 2H), 6.79 (s, 1H), 5.95 (s, 2H), 3.78 (s, 3H); LC-MS method B, (ES+) 350.0, RT=6.91 min.

Workup

  1. extractionextracted into EtOAc
  2. customThe organic phase was collected
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ec5a9cd7f76d40b7b4780f7f7035dd24
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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