Acetone → HCID 16665930, compound

HRID 2366468Notes

Reaction equation

HRID 2366468 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)[CH:5]=[CH:4][C:3]=1[C:13]1[NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([NH2:24])=[O:23])[C:15]=2[N:14]=1.C(N(CC)CC)C.[CH3:32][C:33]([CH3:35])=O.C([BH3-])#N.[Na+]>CO>[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[CH:33]([CH3:35])[CH3:32])[CH:5]=[CH:4][C:3]=1[C:13]1[NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([NH2:24])=[O:23])[C:15]=2[N:14]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 16665853HCID 16665853, compound

Product 1

HCID 16665930HCID 16665930, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of EXAMPLE 50F (80 mg) in methanol (3 mL) was added triethylamine (67 mL) and acetone (35 mL). This solution was stirred at ambient temperature for 1 hour, treated with sodium cyanoborohydride (30 mg), stirred at 50° C. for 18 hours and concentrated. The concentrate was purified by HPLC (Zorbax, C-18, 250×2.54 column, mobile phase A: 0.1% TFA in water; B: 0.1% TFA in CH3CN; 0-100% gradient). 1H NMR (CD3OD) δ 1.33 (d, J=6.71 Hz, 3H), 1.35 (d, J=6.71 Hz, 3H), 2.25-2.34 (m, 3H), 2.58-2.64 (m, 1H), 3.47-3.61 (m, 2H), 3.67-3.74 (m, 1H), 4.72-4.79 (m, 1H), 7.45 (t, J=7.78 Hz, 1H), 7.63 (d, J=8.24 Hz, 1H), 7.66 (d, J=11.90 Hz, 1H), 7.86 (d, J=8.24 Hz, 1H), 8.00 (d, J=7.32 Hz, 1H), 8.48 (t, J=7.78 Hz, 1H).

Workup

  1. stirringstirred at 50° C. for 18 hours
  2. concentrationconcentrated
  3. customThe concentrate was purified by HPLC (Zorbax, C-18, 250×2.54 column, mobile phase A: 0.1% TFA in water; B: 0.1% TFA in CH3CN; 0-100% gradient)

Sources & evidence

ORD record
ord-07c652cc4fa943468935af50d97e83b7
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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