Glycolic Acid → HCID 57524790, compound

HRID 2278793Notes

Reaction equation

HRID 2278793 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:27]=[C:26]([CH3:28])[C:20]([O:21][CH2:22][CH2:23][CH2:24][NH2:25])=[C:19]([CH2:29][CH3:30])[CH:18]=4)[N:13]=3)[CH:9]=[C:8]([O:31][CH3:32])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:33](O)(=[O:36])[CH2:34][OH:35].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.CC(=O)OCC>[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:27]=[C:26]([CH3:28])[C:20]([O:21][CH2:22][CH2:23][CH2:24][NH:25][C:34](=[O:35])[CH2:33][OH:36])=[C:19]([CH2:29][CH3:30])[CH:18]=4)[N:13]=3)[CH:9]=[C:8]([O:31][CH3:32])[N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 757Glycolic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 70558665HCID 70558665, compound

Product 1

HCID 57524790HCID 57524790, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)propan-1-amine (200 mg, 0.458 mmol), glycolic acid (52 mg, 0.687 mmol) and DIPEA (178 mg, 1.37 mmol) in DMF (5 mL), TBTU (191 mg, 0.596 mmol) is added. The mixture is stirred at rt for 18 h before it is diluted with EA (50 mL) and washed twice with sat. aq. NaHCO3 solution (50 mL) followed by brine (50 mL). The org. extract is dried over Na2SO4, filtered, and concentrated. The crude product is purified by prep. HPLC to give the title compound (116 mg) as a pale yellow oil; LC-MS: tR=1.14 min, [M+H]+=495.25; 1H NMR (CD3OD): δ 7.85 (s, 1H), 7.83 (s, 1H), 7.53 (s, 1H), 7.28 (s, 1H), 4.01 (s, 2H), 4.00 (s, 3H), 3.94 (t, J=6.1 Hz, 2H), 3.57 (t, J=6.9 Hz, 2H), 3.24-3.31 (m, 1H), 2.77 (q, J=7.6 Hz, 2H), 2.38 (s, 3H), 2.05-2.16 (m, 4H), 1.86-1.96 (m, 4H), 1.72-1.82 (m, 2H), 1.31 (t, J=7.5 Hz, 3H).

Workup

  1. washwashed twice with sat. aq. NaHCO3 solution (50 mL)
  2. extractionextract
  3. dry with materialis dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by prep

Sources & evidence

ORD record
ord-e699c2f0e6d84e3eb876d3f77fc21480
Source dataset
uspto-grants-2015_09
Patent number
US09133179B2

Reaction notes

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