Ethanol → HCID 58204027, compound

HRID 1190493Notes

Reaction equation

HRID 1190493 reaction equation
[F:1][C:2]([F:27])([F:26])[CH2:3][N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([C:23](=[O:25])[CH3:24])[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][CH:6]=[N:5]1.C(O)C.[BH4-].[Na+]>>[F:26][C:2]([F:1])([F:27])[CH2:3][N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([CH:23]([OH:25])[CH3:24])[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][CH:6]=[N:5]1

Participants

4

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 67050571HCID 67050571, compound

Product 1

HCID 58204027HCID 58204027, compoundYield 31.6%

Procedure

To a solution of 1-{2-[2-(2,2,2-Trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl}-ethanone (0.2357 g, 0.0005976 mol) in ethanol (2.5 mL, 0.043 mol) was added sodium tetrahydroborate (0.02713 g, 0.0007172 mol). The reaction was stirred at room temperature for 5 hours. The reaction was quenched with 2N HCl and diluted with water. Ethyl acetate was added and the aqueous layer was extracted 3× with ethyl acetate. The organic phases were combined, dried with MgSO4, and concentrated. The crude was purified by reverse-phase HPLC to give 292 (74.8 mg) as a white solid. MS (ESI+) 397.0. 1H NMR (400 MHz, DMSO) δ 8.28 (s, 1H), 8.25 (d, J=8.2, 1H), 7.16 (dd, J=8.2, 1.1, 1H), 7.05 (m, 1H), 5.85 (q, J=8.7, 2H), 5.19 (d, J=4.4, 1H), 4.79-4.63 (m, 1H), 4.36 (t, J=5.0, 2H), 3.45 (t, J=5.0, 2H), 1.34 (d, J=6.4, 3H)

Workup

  1. customThe reaction was quenched with 2N HCl
  2. additiondiluted with water
  3. additionEthyl acetate was added
  4. extractionthe aqueous layer was extracted 3× with ethyl acetate
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. customThe crude was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-189e2e2cd8634898822c3abc7f8c425b
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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