Water → HCID 68691118, compound

HRID 1991408Notes

Reaction equation

HRID 1991408 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([C@H:13]3[CH2:18][CH2:17][CH2:16][CH2:15][N:14]3[C:19](=[O:28])[CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.[C:38](Cl)(=[O:40])[CH3:39].O>C1COCC1>[O:21]([CH2:20][C:19]([N:14]1[CH2:15][CH2:16][CH2:17][CH2:18][C@@H:13]1[C:11]1[O:10][N:9]=[C:8]([C:4]2[CH:3]=[C:2]([NH:1][C:38](=[O:40])[CH3:39])[CH:7]=[CH:6][CH:5]=2)[N:12]=1)=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 68688833HCID 68688833, compound

Product 1

HCID 68691118HCID 68691118, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

1 mmol (R)-1-{2-[3-(3-Amino-phenyl)-[1,2,4]oxadiazol-5-yl]-piperidin-1-yl}-2-phenoxy ethanone were dissolved in THF. 2 eq. of DIPEA were added. The reaction was cooled to 0° C. 1 eq. of acetylchloride in THF was added dropwise and the reaction stirred for 30 min. The product was isolated by extraction from ethylactetade/water and subsequent purification via preparative HPLC.

Sources & evidence

ORD record
ord-0a0dc82867c040f696aa52b51d148caf
Source dataset
uspto-grants-2010_01
Patent number
US07645776B2

Reaction notes

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