Acetone → HCID 71610222, compound

HRID 1479069Notes

Reaction equation

HRID 1479069 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[N:9][C:8]2[N:4]([N:5]=[C:6]3[CH2:14][N:13]([C:15]([C:17]4[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=4[O:24][CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[O:16])[CH2:12][C:7]3=2)[C:3]=1[CH3:31].[CH3:32][C:33]([CH3:35])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:10]([CH3:11])=[N:9][C:8]2[N:4]([N:5]=[C:6]3[CH2:14][N:13]([C:15]([C:17]4[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=4[O:24][CH:25]4[CH2:30][CH2:29][N:28]([CH:33]([CH3:35])[CH3:32])[CH2:27][CH2:26]4)=[O:16])[CH2:12][C:7]3=2)[C:3]=1[CH3:31]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 71610191HCID 71610191, compound

Product 1

HCID 71610222HCID 71610222, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of Example 64 (110 mg; 0.25 mmol; 1 eq.), acetone (109 μL; 1.49 mmol; 6 eq.) and sodium triacetoxyborohydride (210 mg; 0.99 mmol; 4 eq.) in DCM (6 mL) was stirred at room temperature for 60 hours. The reaction mixture was diluted with DCM, washed with sat. aq. NaHCO3, dried over sodium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (68 mg, 56%) as a yellow powder. 1H NMR (CDCl3) δ 7.33 (td, J=8.2, 6.7 Hz, 1H), 6.80-6.63 (m, 2H), 5.05-4.91 (m, 2H), 4.67 (br s, 2H), 4.36 (br s, 1H), 2.91 (s, 2H), 2.86 (s, 1H), 2.78-0.52 (m, 6H), 2.46-2.24 (m, 2H), 2.06-1.88 (m, 2H), 1.88-1.70 (m, 2H), 0.94 (d, J=6.5 Hz, 6H). HPLC (max plot) 94.1%, Rt 3.02 min. UPLC/MS: (MS+) 486.5 ([M+H]+).

Workup

  1. washwashed with sat. aq. NaHCO3
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by mass

Sources & evidence

ORD record
ord-4c19052352324263b0b455142f8d5615
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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