Water → HCID 86704023, compound

HRID 1773932Notes

Reaction equation

HRID 1773932 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][C:12]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:13]3[C:23](O)=[O:24])[CH2:4][CH2:3]1.O>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][C:12]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[C:13]3[CH2:23][OH:24])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 962WaterHCID 86704021HCID 86704021, compound

Product 1

HCID 86704023HCID 86704023, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(1-methylpiperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-1-carboxylic acid (example 256B) (50 mg, 0.120 mmole) in THF (2 mL) is added dropwise BH3-Me2S (46 μL, 0.48 mmole). The reaction mixture is heated at 50° C. overnight. Water is added and the aqueous phase is extracted with AcOEt. The organic phase is dried over MgSO4, filtered and the solvent removed under reduced pressure. The residue is purified by silica gel chromatography eluting with (CH2Cl2:MeOH) from (100:0) to (90:10) to give [4-(1-methylpiperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-1-yl]-methanol melting at 120° C.

Workup

  1. extractionthe aqueous phase is extracted with AcOEt
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe residue is purified by silica gel chromatography
  6. washeluting with (CH2Cl2:MeOH) from (100:0) to (90:10)

Sources & evidence

ORD record
ord-0ad3f054bf22416b87fb307083121439
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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