Acetic Acid → HCID 178524299, compound

HRID 510402Notes

Reaction equation

HRID 510402 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[C:10]([N:23]3[C:31](=[O:32])[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]3=[O:33])[C:11]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)=[C:4]2[N:3]=1.[OH-:34].[Na+].[OH2:36].C(O)(=O)C>O1CCCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([OH:34])[N:5]2[N:9]=[C:10]([NH:23][C:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=3[C:31]([OH:36])=[O:32])=[O:33])[C:11]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)=[C:4]2[N:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86724883HCID 86724883, compound

Product 1

HCID 178524299HCID 178524299, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[5,7-dichloro-3-(1-naphthalenylmethyl)pyrazolo[1,5-a]pyrimidin-2-yl]-1H-isoindole-1,3(2H)-dione (2.1 g, 4.44 mmol) in Tetrahydrofuran (THF) (60 mL) was added in sodium hydroxide (26.6 mL, 26.6 mmol). The reaction mixture was stirred at rt for 18 h. Water (20 mL) and EtOAc (60 mL) was added in. The reaction was acidified with acetic acid (2.54 mL, 44.4 mmol). The aqueous phase was extracted with EtOAc (60 mL×2). The combined organic phases were washed with brine (30 mL), dried (MgSO4) and concentrated. The crude was used for the next step. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.37 (s, 2H) 5.31 (s, 1H) 7.21 (s, 2H) 7.33 (m, 1H) 7.46 (m, 4H) 7.72 (m, 2H) 7.82-7.97 (m, 1H) 8.35 (m, 1H); LC/MS: MS (ES+) m/e 473.1 [M+H]+.

Workup

  1. extractionThe aqueous phase was extracted with EtOAc (60 mL×2)
  2. washThe combined organic phases were washed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0d9080509bc1433a817254660bc96264
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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