HCID 59656523, compound → HCID 59656330, compound

HRID 561323Notes

Reaction equation

CON(C)[C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([S:16](=[O:32])(=[O:31])[NH:17][CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:20][CH2:19]2)=[CH:8][CH:7]=1)=[O:5].[CH3:34][Mg]Br>C1COCC1>[CH2:24]([N:21]1[CH2:20][CH2:19][CH:18]([NH:17][S:16]([C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]([C:4](=[O:5])[CH3:34])=[CH:7][CH:8]=2)(=[O:32])=[O:31])[CH2:23][CH2:22]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a 0° C. solution of 4-(1-benzyl-piperidin-4-ylsulfamoyl)-naphthalene-1-carboxylic acid methoxy-methyl-amide 35 (200 mg, 0.43 mmol) in THF (5 mL) was slowly added methylmagnesium bromide (5.71 mL, 17.1 mmol, IM THF solution). After stirring at 25° C. for 4 h, the resultant mixture was quenched with saturated ammonium chloride solution. The aqueous layer was extracted with CH2Cl2. The organic extracts were combined, washed with brine and dried over MgSO4. The solution was filtered and concentrated in vacuo to give the crude product. The crude material was purified by Flash column chromatography (hexane/EtOAc) to provide 118 mg of 4-acetyl-naphthalene-1-sulfonic acid (1-benzyl-piperidin-4-yl)-amide 36 in 56% overall yield (for two steps). LCMS showed m/z: 423 (M+H)+.

Workup

customTo a 0° C.
customthe resultant mixture was quenched with saturated ammonium chloride solution
extractionThe aqueous layer was extracted with CH2Cl2
washwashed with brine
dry with materialdried over MgSO4
filtrationThe solution was filtered
concentrationconcentrated in vacuo
customto give the crude product
customThe crude material was purified by Flash column chromatography (hexane/EtOAc)

Sources & evidence

ORD record: ord-9e7cb4fb26e44e2da7d99aa25f0b3d1a
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063222B2

Reaction notes

Loading…