Sodium borohydride → HCID 86690353, compound

HRID 2409940Notes

Reaction equation

HRID 2409940 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]2[NH:16][C@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]3[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=3)[CH2:18]2)[CH:4]=1)=[O:2].[BH4-].[Na+]>C1COCC1>[OH:2][CH2:1][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]2[NH:16][C@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]3[CH:24]=[CH:25][C:26]([C:27]#[N:28])=[CH:29][CH:30]=3)[CH2:18]2)[CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86690354HCID 86690354, compound

Product 1

HCID 86690353HCID 86690353, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a round bottom flask was added 4-((S)-3-(((1R,2R)-2-((4-formylpyridin-2-yl)amino)cyclohexyl)amino)piperidin-1-yl)benzonitrile (100 mg, 0.248 mmol) and THF (1 mL). The reaction was cooled to 0° C. and NaBH4 (9.38 mg, 0.248 mmol) was added to the reaction. The reaction was stirred at 0° C. for 2 hrs. The reaction was quenched with 1N NH4Cl (0.5 ml) and then diluted with EtOAc (30 ml). The organics was washed with water (2×15 ml) and saturated NaCl solution (15 ml). The organic layer dried over MgSO4, filtered and concentrated. The residue was purified using ISCO system (0-100% EtOAc/Hex) to give 4-((S)-3-(((1R,2R)-2-((4-(hydroxymethyl)pyridin-2-yl)amino)cyclohexyl)amino)piperidin-1-yl)benzonitrile (23 mg, 0.054 mmol, 21.74% yield) as white solid. Anal. Calcd. for C24H31N5O m/z 405.3, found: 406.2 (M+H)+; 1H NMR (400 MHz, METHANOL-D4) δ ppm 8.07-7.97 (m, 1H), 7.45 (d, J=8.8 Hz, 2H), 6.93 (d, J=9.3 Hz, 3H), 6.62-6.51 (m, 1H), 4.60 (s, 2H), 3.86-3.75 (m, 1H), 3.71-3.62 (m, 1H), 3.37-3.33 (m, 1H), 2.95-2.84 (m, 1H), 2.83-2.59 (m, 3H), 2.16-2.04 (m, 2H), 2.01-1.92 (m, 1H), 1.82-1.72 (m, 2H), 1.68-1.55 (m, 1H), 1.45-1.23 (m, 6H).

Workup

  1. customThe reaction was quenched with 1N NH4Cl (0.5 ml)
  2. additiondiluted with EtOAc (30 ml)
  3. washThe organics was washed with water (2×15 ml) and saturated NaCl solution (15 ml)
  4. dry with materialThe organic layer dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-5c7349af0beb4d29b67ebadf1607dd0b
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

Loading…