HCID 70558026, compound → HCID 57524378, compound

HRID 2278781Notes

Reaction equation

HRID 2278781 reaction equation
[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:33]=[C:32]([CH3:34])[C:20]([O:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])=[C:19]([CH2:35][CH3:36])[CH:18]=4)[N:13]=3)[CH:9]=[C:8]([O:37][CH3:38])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.C1COCC1.[Li+].[OH-]>[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:33]=[C:32]([CH3:34])[C:20]([O:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[C:19]([CH2:35][CH3:36])[CH:18]=4)[N:13]=3)[CH:9]=[C:8]([O:37][CH3:38])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 70558026HCID 70558026, compound

Product 1

HCID 57524378HCID 57524378, compoundYield 75.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 3-((2-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methyl-phenoxy)ethyl)amino)propanoate (88 mg, 0.168 mmol) in MeOH (0.5 mL), THF (0.5 mL) and 2 N aq. LiOH (0.2 mL) is stirred at rt for 2 h. The mixture is concentrated, diluted with 2 N aq. HCl (10 mL) and extracted four times with DCM (4×20 mL). The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by prep. HPLC to give the title compound (63 mg) as an off-white solid; LC-MS: tR=0.93 min, [M+H]+=495.12; 1H NMR (CDCl3): δ 8.37 (s br, 2H), 7.78 (s, 1H), 7.72 (s, 1 H), 7.43 (s, 1H), 7.20 (s, 1H), 4.07-4.18 (m, 2H), 3.99 (s, 3H), 3.34-3.42 (m, 2H), 3.16-3.34 (m, 3H), 2.62-2.76 (m, 4H), 2.33 (s, 3H), 2.09 (m, 2H), 1.81-1.94 (m, 4H), 1.68-1.79 (m, 2H), 1.27 (t, J=7.5 Hz, 3H).

Workup

  1. concentrationThe mixture is concentrated
  2. additiondiluted with 2 N aq. HCl (10 mL)
  3. extractionextracted four times with DCM (4×20 mL)
  4. dry with materialextracts are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by prep

Sources & evidence

ORD record
ord-35668d26075f4916b541ead45bb2f7a8
Source dataset
uspto-grants-2015_09
Patent number
US09133179B2

Reaction notes

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