Methanesulfonamide → HCID 67110988, compound

HRID 537356Notes

Reaction equation

HRID 537356 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][CH2:21][C:22]([OH:24])=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:25].OC1C=CC=CC=1C1(C#N)CCNCC1.[CH3:41][S:42]([NH2:45])(=[O:44])=[O:43].CCN=C=NCCCN(C)C.Cl>C1COCC1.C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[ClH:25].[CH3:41][S:42]([NH:45][C:22](=[O:24])[CH2:21][CH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)(=[O:44])=[O:43]

Participants

8

Reactant 4

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 497606741-(1,1-Dimethylethyl) 4-[2-(2-carboxyethyl)phenyl]-1-piperidinecarboxylateHCID 86669375HCID 86669375, compound

Product 1

HCID 67110988HCID 67110988, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

Acid 3-(2-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)propanoic acid obtained in step 1 of representative example 8 (40 mg, 0.12 mmol) and methane sulfonamide (17 mg, 0.18 mmol) were dissolved in THF/CH2Cl2 (0.5 mL/1.0 mL). DMAP (22 mg, 0.18 mmol) and EDC.HCl (35 mg, 0.18 mmol) were added and the reaction was stirred at 23° C. overnight. Water was added to the reaction mixture and was extracted with EtOAc (2×10 mL). The organic layers were dried over Na2SO4 and concentrated.

Workup

  1. extractionwas extracted with EtOAc (2×10 mL)
  2. dry with materialThe organic layers were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e60b1d47e28049a98c71488005f58077
Source dataset
uspto-grants-2014_10
Patent number
US08859776B2

Reaction notes

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