Acetaldehyde → HCID 16665854, compound

HRID 2366467Notes

Reaction equation

HRID 2366467 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.[CH2:25](N(CC)CC)[CH3:26].C(=O)C.C([BH3-])#N.[Na+]>CO.O>[CH2:25]([N:9]1[CH2:10][CH2:11][CH2:12][CH:8]1[C:6]1[CH:5]=[CH:4][C:3]([C:13]2[NH:17][C:16]3[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([NH2:24])=[O:23])[C:15]=3[N:14]=2)=[C:2]([F:1])[CH:7]=1)[CH3:26]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 16665853HCID 16665853, compound

Product 1

HCID 16665854HCID 16665854, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of EXAMPLE 50F (150 mg) in methanol (6 mL) was added triethylamine (125 mL) and 32 wt/v % acetaldehyde in water (210 mL). The solution was stirred for 1 hour, treated with sodium cyanoborohydride (95 mg), stirred for 3 hours at ambient temperature and 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 1.31-1.36 (m, 3H), 2.30-2.42 (m, 2H), 2.61-2.70 (m, 1H), 3.17-3.29 (m, 2H), 3.34-3.41 (m, 1H), 3.52-3.62 (m, 1H), 3.94-4.01 (m, 1H), 4.64-4.73 (m, 1H), 7.75 (t, J=7.98 Hz, 1H), 7.87 (d, J=7.67 Hz, 1H), 7.93 (d, J=11.35 Hz, 1H), 8.07 (d, J=7.98 Hz, 1H), 8.13 (d, J=7.67 Hz, 1H), 8.28 (t, J=7.52 Hz, 1H).

Workup

  1. stirringstirred for 3 hours at ambient temperature and 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-224807723ac14450953aaf1225ec28d7
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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