Acetic Acid → HCID 11214431, compound

HRID 1592067Notes

Reaction equation

HRID 1592067 reaction equation
NO.[NH2:3][C:4]1[C:5]2[S:12][C:11]3[N:13]=[C:14]([N:20]4[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]4)[CH:15]=[C:16]([CH2:17][CH2:18][CH3:19])[C:10]=3[C:6]=2[N:7]=[CH:8][N:9]=1.[C:27]([BH3-])#[N:28].[C:30](O)(=O)[CH3:31].CN([CH:37]=[O:38])C>>[NH2:3][C:4]1[C:5]2[S:12][C:11]3[N:13]=[C:14]([N:20]4[CH2:25][CH2:24][CH:23]([NH:28][CH2:27][CH:37]([C:4]5[C:30]6[C:31](=[CH:14][CH:15]=[CH:16][CH:17]=6)[CH:10]=[CH:6][CH:5]=5)[OH:38])[CH2:22][CH2:21]4)[CH:15]=[C:16]([CH2:17][CH2:18][CH3:19])[C:10]=3[C:6]=2[N:7]=[CH:8][N:9]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 787HydroxylamineHCID 6228DimethylformamideHCID 498716Cyano-borohydrideHCID 11416569HCID 11416569, compound

Product 1

HCID 11214431HCID 11214431, compound

Procedure

The above amino alcohol (200 mg, 0.586 mmol) and 1-(4-amino-9-propyl -pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-7-yl)-piperidin-4-one (Example 4) (200 mg, 0.894 mmol) was dissolved in 10 mL of dry DMF. MP-Cyanoborohydride (375 mg, 0.884 mmol) was added followed by glacial acetic acid (0.3 mL). This mixture was shaken for 16 h. The resin was removed by filtration and washed with MeOH and dichloromethane. The filtrate was evaporated. The residue was treated with 2 M sodium carbonate solution. The resulting solid was collected by filtration and recrystalized from MeOH/acetonitrile to give the title compound as a pale-colored solid. Yield: 189 mg, 63%.

Workup

  1. customThe resin was removed by filtration
  2. washwashed with MeOH and dichloromethane
  3. customThe filtrate was evaporated
  4. additionThe residue was treated with 2 M sodium carbonate solution
  5. filtrationThe resulting solid was collected by filtration
  6. customrecrystalized from MeOH/acetonitrile

Sources & evidence

ORD record
ord-359ca6a0c7fd40408dfe37bcf5c67428
Source dataset
uspto-grants-2007_11
Patent number
US07291733B2

Reaction notes

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