Cyclobutanesulfonamide → HCID 67999193, compound

HRID 1048545Notes

Reaction equation

HRID 1048545 reaction equation
[CH2:1]([C@@:4]1([CH3:30])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:27][CH3:28])[CH2:25]O)[C:5]1=[O:29])[CH:2]=[CH2:3].[CH:31]1([S:35]([NH2:38])(=[O:37])=[O:36])[CH2:34][CH2:33][CH2:32]1>>[CH2:1]([C@@:4]1([CH3:30])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:27][CH3:28])[CH2:25][NH:38][S:35]([CH:31]2[CH2:34][CH2:33][CH2:32]2)(=[O:37])=[O:36])[C:5]1=[O:29])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 15238957CyclobutanesulfonamideHCID 58573282(3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)-3-methylpiperidin-2-one

Product 1

HCID 67999193HCID 67999193, compound

Conditions

Temperature
40 °C

Procedure

The title compound was prepared from (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)-3-methylpiperidin-2-one (Example 91, Step B, 250 mg, 0.560 mmol) and cyclobutanesulfonamide (Example 271G, 256 mg, 1.894 mmol) using the general procedure described in Step A of Example 272, albeit with an oil bath heated at 40° C. The crude product was purified by silica gel chromatography eluting with a gradient of EtOAc in hexanes. The product was obtained as a white powder (220 mg, 70%). LCMS (ESI): m/z=563.2 (M+H).

Workup

  1. customdescribed in Step A of Example 272, albeit with an oil bath
  2. customThe crude product was purified by silica gel chromatography
  3. washeluting with a gradient of EtOAc in hexanes

Sources & evidence

ORD record
ord-e8498276ccff4d8a8b6a2147343d4d41
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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