HCID 118062339, compound → HCID 118061887, compound

HRID 920823Notes

Reaction equation

HRID 920823 reaction equation
[I:1][C:2]1[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:5]2[C:6](=O)[NH:7][CH:8]([C:10]([F:13])([F:12])[F:11])[CH2:9][N:4]2[N:3]=1>C1COCC1>[I:1][C:2]1[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:5]2[CH2:6][NH:7][CH:8]([C:10]([F:12])([F:11])[F:13])[CH2:9][N:4]2[N:3]=1

Participants

3

Reactant 1

HCID 118062339HCID 118062339, compound

Product 1

HCID 118061887HCID 118061887, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Intermediate 346B (0.1 g, 0.248 mmol) in THF (1 mL) was added BH3.DMS complex (0.236 mL, 2.481 mmol) under nitrogen and the reaction mixture was stirred at RT for 16 h. The reaction mixture was then cooled to 0° C., quenched with methanol (1 mL) and stirred for 15 min at RT. The volatiles were removed under reduced pressure and the crude compound was purified by silica gel chromatography (12 g REDISEP® column, eluting with 25% EtOAc in hexanes). Fractions containing the product were combined and evaporated to afford Intermediate 346C as a white solid (0.025 g, 25%). MS(ES): −m/z=390.4 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 4.37-4.27 (m, 2H), 4.22 (q, J=7.4 Hz, 3H), 4.12-4.00 (m, 3H), 1.33-1.26 (m, 3H).

Workup

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. customquenched with methanol (1 mL)
  3. stirringstirred for 15 min at RT
  4. customThe volatiles were removed under reduced pressure
  5. customthe crude compound was purified by silica gel chromatography (12 g REDISEP® column, eluting with 25% EtOAc in hexanes)
  6. additionFractions containing the product
  7. customevaporated

Sources & evidence

ORD record
ord-bdcfae26ef5341c4a67631858b6cef3d
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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