Lithium borohydride → HCID 67325905, compound

HRID 1397473Notes

Reaction equation

HRID 1397473 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:12]3([CH2:18][NH:19][C:20]([C:22]4[CH:23]=[C:24]([C:28]5[N:32]=[C:31]([C:33](OCC)=[O:34])[O:30][N:29]=5)[CH:25]=[CH:26][CH:27]=4)=[O:21])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Li+]>C1COCC1>[OH:34][CH2:33][C:31]1[O:30][N:29]=[C:28]([C:24]2[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=2)[C:20]([NH:19][CH2:18][C:12]2([C:9]3[S:10][CH:11]=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[N:8]=3)[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[O:21])[N:32]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 67323825HCID 67323825, compound

Product 1

HCID 67325905HCID 67325905, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 3-(3-(((4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methyl)carbamoyl)phenyl)-1,2,4-oxadiazole-5-carboxylate (1.0 g, 1.93 mmol) was dissolved in anhydrous THF (20 mL) and the reaction mixture was cooled to 0° C. Lithium borohydride (1.15 mL, 2.3 mmol, 2M in THF) was added, and the reaction mixture was stirred for 30 min, quenched with ice, and diluted with EtOAc. The organic layer was washed with water and brine, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluant: 70-80% EtOAc in petroleum ether) to afford 3-(5-(hydroxymethyl)-1,2,4-oxadiazol-3-yl)-N-((4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methyl)benzamide (300 mg, yield 32%). 1H NMR (300 MHz, DMSO-d6) δ 8.46 (m, 1H), 8.20-8.17 (m, 1H), 7.96 (m, 1H), 7.91-7.88 (m, 2H), 7.62 (m, 1H), 7.53-7.51 (m, 2H), 7.36-7.34 (m, 3H), 4.89 (s, 2H), 3.99-3.92 (m, 2H), 3.90-3.88 (d, J=5.7 Hz, 2H), 3.78-3.70 (m, 2H), 2.35-2.27 (m, 2H), 2.08-2.00 (m, 2H). MS (ESI) m/z: Calculated for C26H24N4O4S: 476.15. found: 475.7 (M−H)−.

Workup

  1. customquenched with ice
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (silica gel 60-120 mesh, eluant: 70-80% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-6b10fb91fe3b45989875ed3d9db5ea73
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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