Water → HCID 86703991, compound

HRID 1773912Notes

Reaction equation

HRID 1773912 reaction equation
[CH3:1][C:2]1[N:11]2[C:5]([CH:6]([O:16][CH:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10]2)=[N:4][C:3]=1[C:24]1[CH:38]=[CH:37][C:27]([C:28]([N:30]2[CH2:35][CH2:34][C:33](=[O:36])[CH2:32][CH2:31]2)=[O:29])=[CH:26][CH:25]=1.[BH4-].[Na+].O>CO>[OH:36][CH:33]1[CH2:34][CH2:35][N:30]([C:28]([C:27]2[CH:26]=[CH:25][C:24]([C:3]3[N:4]=[C:5]4[N:11]([CH2:10][CH2:9][C:8]5[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=5[CH:6]4[O:16][CH:17]4[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]4)[C:2]=3[CH3:1])=[CH:38][CH:37]=2)=[O:29])[CH2:31][CH2:32]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86703992HCID 86703992, compound

Product 1

HCID 86703991HCID 86703991, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-{4-[1-methyl-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-2-yl]-benzoyl}-piperidin-4-one (example 218) (93.7 mg, 0.183 mmole) in MeOH (2 mL) is added portionwise NaBH4 (10.5 mg, 0.275 mmole). After 2 hours at room temperature, water is added and the aqueous phase is extracted with AcOEt. AcOEt phase is dried over MgSO4, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography eluting with (CH2Cl2:MeOH) (90:1) then (CH2Cl2:MeOH:NH4OH) (9:1:0.1). The residual solid is triturated three times with Et2O to give (4-hydroxypiperidin-1-yl)-{4-[1-methyl-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-2-yl]-phenyl}-methanone.

Workup

  1. extractionthe aqueous phase is extracted with AcOEt
  2. dry with materialAcOEt phase is dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent is removed under reduced pressure
  5. customThe residue is purified by silica gel chromatography
  6. washeluting with (CH2Cl2:MeOH) (90:1)
  7. customThe residual solid is triturated three times with Et2O

Sources & evidence

ORD record
ord-09957fe2759b4fc19d23bf57d8ffac0e
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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