Acetic Acid → HCID 59592985, compound

HRID 2098708Notes

Reaction equation

HRID 2098708 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.C1C=C[NH+]=CC=1.Br[Br-]Br.C(O)(=[O:36])C>O>[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][C:2](=[O:36])[NH:1]4)[N:11]=2)[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 176Acetic Acid2×HCID 59592817HCID 59592817, compound

Product 1

HCID 59592985HCID 59592985, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(1H-Indol-4-yl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine 199 (90 mg) in acetic acid (2 ml) and water (1 ml) was added pyridinium bromide perbromide (103 mg) as a solution in acetic acid (4 ml) and the reaction mixture was heated to 80° C. for 4 hours. The mixture was then basified and extracted into dichloromethane, organic layer was dried (Mg2SO4), filtered and volatiles removed in vacuo. Purification on silica yielded 198 (23 mg). NMR: (CDCl3): 3.39-3.43 (4H, m), 4.03-4.08 (4H, m), 4.10 (2H, s), 6.95 (1H, d, J=7.4), 7.36 (1H, t, J=7.9), 7.49 (2H, m), 7.79 (1H, d, J=5.6), 8.10 (1H, d, J=7.9) MS: (ESI+): MH+ 353 (100%)

Workup

  1. extractionextracted into dichloromethane, organic layer
  2. dry with materialwas dried (Mg2SO4)
  3. filtrationfiltered
  4. customvolatiles removed in vacuo
  5. customPurification on silica

Sources & evidence

ORD record
ord-499ff49fe8054b388e4f04ef98cd0f04
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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