Formic Acid → HCID 9843816, compound

HRID 375868Notes

Reaction equation

HRID 375868 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([O:24][CH2:25][CH:26]1[O:28][CH2:27]1)=[CH:11][CH:10]=3)[CH3:2].C(O)=[O:30]>>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([O:24][CH2:25][CH:26]([OH:28])[CH2:27][OH:30])=[CH:11][CH:10]=3)[CH3:2]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 86749231HCID 86749231, compound

Product 1

HCID 9843816HCID 9843816, compound

Procedure

A mixture of 1-ethyl-6-(2,3-epoxypropoxy)-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine (0.53 g) and formic acid (10 ml) were stirred at room temperature overnight. The excess formic acid was removed in vacuo and then methanol (75 ml) and triethylamine (10 ml) were added and the mixture was stirred for four hours. The reaction mixture was evaporated, ether was added and the product which crystallized was recrystallized from CH2Cl2 /Et2O and then purified by column chromatography on silca eluting with CH2Cl2 /THF (1/1) to afford 1-ethyl-6-(2,3-dihydroxypropoxy)-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, m.p. 197°-199° C.

Workup

  1. customThe excess formic acid was removed in vacuo
  2. additionmethanol (75 ml) and triethylamine (10 ml) were added
  3. stirringthe mixture was stirred for four hours
  4. customThe reaction mixture was evaporated
  5. additionether was added
  6. customthe product which crystallized
  7. customwas recrystallized from CH2Cl2 /Et2O
  8. custompurified by column chromatography on silca
  9. washeluting with CH2Cl2 /THF (1/1)

Sources & evidence

ORD record
ord-f7f90603718f4f8a88fac9d119444d0f
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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