Sodium borohydride → HCID 71136251, compound

HRID 1468845Notes

Reaction equation

HRID 1468845 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([C@H:15]3[CH2:17][C@H:16]3[CH2:18][O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH:28]=[O:29])=[CH:23][CH:22]=3)[CH2:11][CH2:10]2)=[N:7][CH:8]=1)[CH3:2].[BH4-].[Na+]>C(Cl)Cl.CO>[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:10][CH2:11][CH:12]([C@H:15]3[CH2:17][C@H:16]3[CH2:18][O:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([CH2:27][CH2:28][OH:29])=[CH:25][CH:26]=3)[CH2:13][CH2:14]2)=[N:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86717792HCID 86717792, compound

Product 1

HCID 71136251HCID 71136251, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
0 °C

Procedure

The product of step B (70 mg, 0.18 mmol) was dissolved in DCM/MeOH (1/1, 4 mL) at 0° C., and sodium borohydride (30 mg, 0.8 mmol) added. The solution was stirred at 0° C. for 1 h. The solution was partitioned between water and DCM. The aqueous layer was extracted with DCM. The combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was purified via silica gel column chromatography (2/1 hexanes/EtOAc) followed by reverse phase HPLC (C18, 10-100% water/acetonitrile with 0.1% formic acid gradient) which yielded the title compound. MS (ESI) m/z 396 [M+H]+. GPR119 Human EC50: 2.5 nM

Workup

  1. customThe solution was partitioned between water and DCM
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via silica gel column chromatography (2/1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-3a0b88fcaeaa485e922181a1b3b09cfe
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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