Acetic Acid → HCID 59592841, compound

HRID 2262142Notes

Reaction equation

HRID 2262142 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:11]=[C:12]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[C:13]4[S:18][CH:17]=[CH:16][C:14]=4[N:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([BH3-])#N.[Na+].[C:29](O)(=[O:31])[CH3:30]>>[O:22]1[CH2:21][CH2:20][N:19]([C:12]2[C:13]3[S:18][CH:17]=[CH:16][C:14]=3[N:15]=[C:10]([C:5]3[CH:6]=[CH:7][CH:8]=[C:9]4[C:4]=3[CH2:3][CH2:2][N:1]4[C:29](=[O:31])[CH3:30])[N:11]=2)[CH2:24][CH2:23]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 59592817HCID 59592817, compound

Product 1

HCID 59592841HCID 59592841, compound

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(1H-Indol-4-yl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine 199 (100 mg) in acetic acid (2 ml) was added sodium cyanoborohydride (76 mg) and the reaction mixture was heated at 60° C. overnight. The mixture was then basified and extracted into dichloromethane, organic layer was dried (Mg2SO4), filtered and volatiles removed in vacuo. Flash chromatography and recrystallization from hot dichloromethane/hexane gave 228 (11 mg). NMR: (DMSOd6): 2.21 (3H, s), 3.70 (2H, t, J=8.6), 3.80-3.86 (4H, m), 3.98-4.04 (4H, m), 4.17 (2H, t, J=8.5), 7.30 (1H, t, J=7.9), 7.55 (1H, d, J=5.6), 8.00 (1H, d, J=8.4), 8.25 (1H, d, J=7.8), 8.30 (1H, d, J=5.6) MS: (ESI+): MH+ 381

Workup

  1. extractionextracted into dichloromethane, organic layer
  2. dry with materialwas dried (Mg2SO4)
  3. filtrationfiltered
  4. customvolatiles removed in vacuo
  5. customFlash chromatography and recrystallization from hot dichloromethane/hexane

Sources & evidence

ORD record
ord-01598fa7fd8e46bbaf192f5272f72bd9
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

Loading…