Hydrochloric Acid → HCID 136333916, compound

HRID 1022915Notes

Reaction equation

HRID 1022915 reaction equation
O1[C:5]2([CH2:9][CH2:8][N:7]([CH2:10][C:11]3[NH:12][C:13](=[O:26])[C:14]4[S:19][C:18]([C:20]5[CH:21]=[N:22][NH:23][C:24]=5[CH3:25])=[CH:17][C:15]=4[N:16]=3)[CH2:6]2)[O:4]CC1.Cl.C(=O)([O-])O.[Na+]>CC(O)C>[CH3:25][C:24]1[NH:23][N:22]=[CH:21][C:20]=1[C:18]1[S:19][C:14]2[C:13](=[O:26])[NH:12][C:11]([CH2:10][N:7]3[CH2:8][CH2:9][C:5](=[O:4])[CH2:6]3)=[N:16][C:15]=2[CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 136333917HCID 136333917, compound

Product 1

HCID 136333916HCID 136333916, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(1,4-dioxa-7-azaspiro[4.4]non-7-ylmethyl)-6-(5-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3H)-one (150 mg) produced in Example 39, step D, 6M hydrochloric acid (3 mL) and propan-2-ol (3 mL) was stirred with heating at 90° C. for 5 hr. Saturated aqueous sodium hydrogen carbonate (20 mL) was added to the reaction mixture, and the precipitated solid was collected by filtration, and washed successively with ethyl acetate (3 mL) and water (3 mL). The obtained pale-brown solid was crystallized from methanol/propan-2-ol/hexane to give the title compound (115 mg) as a pale-brown solid.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed successively with ethyl acetate (3 mL) and water (3 mL)
  3. customThe obtained pale-brown solid was crystallized from methanol/propan-2-ol/hexane

Sources & evidence

ORD record
ord-99336061bc964fc2ad5c7fcad2c2f1bc
Source dataset
uspto-grants-2014_05
Patent number
US08722660B2

Reaction notes

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