Formic Acid → HCID 9843816, compound

HRID 1586152Notes

Reaction equation

HRID 1586152 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) are stirred at room temperature overnight. The excess formic acid is removed in vacuo and then methanol (75 ml) and triethylamine (10 ml) are added, and the mixture is stirred for four hours. The reaction mixture is evaporated, ether is added, and the product which crystallizes is 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 is removed in vacuo
  2. additionmethanol (75 ml) and triethylamine (10 ml) are added
  3. stirringthe mixture is stirred for four hours
  4. customThe reaction mixture is evaporated
  5. additionether is added
  6. customthe product which crystallizes
  7. customis recrystallized from CH2Cl2 /Et2O
  8. custompurified by column chromatography on silca
  9. washeluting with CH2Cl2 /THF (1/1)

Sources & evidence

ORD record
ord-aea4a1c7120f42cd80b1ae857fdace68
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

Loading…