Triethylamine → HCID 68578663, compound

HRID 2047323Notes

Reaction equation

HRID 2047323 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:8][NH:7][CH2:6]1)=[O:4].[CH2:9]([N:11]([CH2:38][CH3:39])[C:12]1[CH:17]=[C:16]([C:18]2[O:22][N:21]=[C:20]([C:23]3[CH:28]=[C:27]([CH3:29])[C:26]([O:30][CH2:31][C@@H:32]4[CH2:34][O:33]4)=[C:25]([CH2:35][CH3:36])[CH:24]=3)[N:19]=2)[CH:15]=[C:14]([CH3:37])[N:13]=1)[CH3:10].C(N(CC)CC)C.CC(=O)OCC>CO>[CH3:1][O:2][C:3]([CH:5]1[CH2:8][N:7]([CH2:34][C@H:32]([OH:33])[CH2:31][O:30][C:26]2[C:27]([CH3:29])=[CH:28][C:23]([C:20]3[N:19]=[C:18]([C:16]4[CH:15]=[C:14]([CH3:37])[N:13]=[C:12]([N:11]([CH2:38][CH3:39])[CH2:9][CH3:10])[CH:17]=4)[O:22][N:21]=3)=[CH:24][C:25]=2[CH2:35][CH3:36])[CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 20132751Methyl azetidine-3-carboxylateHCID 86640600HCID 86640600, compound

Product 1

HCID 68578663HCID 68578663, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of azetidine-3-carboxylic acid methyl ester (40 mg, 0.355 mmol) and diethyl-{4-[3-((S)-3-ethyl-5-methyl-4-oxiranylmethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyridin-2-yl}-amine (300 mg, 0.71 mmol, Example 18 step a)) in methanol (5 mL) and triethylamine (0.1 mL) is stirred at 60° C. for 2 days. The mixture is dissolved with EA and washed with sat. aq. NaHCO3-solution. The org. extract is collected and concentrated. The crude product is purified by prep. HPLC to give the title compound (60 mg) as pale yellow oil; LC-MS: tR=0.79 min; [M+1]+=538.04; 1H NMR (CDCl3): δ 1.25 (t, J=6.8 Hz, 6H), 1.32 (t, J=7.5 Hz, 3H), 2.40 (s, 3H), 2.50 (s, 3H), 2.71-2.80 (m, 4H), 3.06 (s br, 1H), 3.35-3.46 (m, 2H), 3.48-3.54 (m, 2H), 3.58-3.72 (m, 6H), 3.75 (s, 3H), 3.81-3.86 (m, 2H), 3.93-4.00 (m, 1H), 7.01 (s, 1H), 7.10 (s, 1H), 7.87 (s, 1H), 7.88 (s, 1H).

Workup

  1. washwashed with sat. aq. NaHCO3-solution
  2. extractionextract
  3. customis collected
  4. concentrationconcentrated
  5. customThe crude product is purified by prep

Sources & evidence

ORD record
ord-e112f62019ea47c6981e9822bc134151
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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