Triethylamine → 4-Methyl-2-(2-(4-(3-(piperidin-1-yl)propoxy)phenyl)acetamido)thiophene-3-carboxamide

HRID 2097990Notes

Reaction equation

HRID 2097990 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=O)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[NH2:28][C:29]1[S:30][CH:31]=[C:32]([CH3:37])[C:33]=1[C:34]([NH2:36])=[O:35].CCN=C=NCCCN(C)C>CN(C=O)C.C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:37][C:32]1[C:33]([C:34]([NH2:36])=[O:35])=[C:29]([NH:28][C:18](=[O:20])[CH2:17][C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[CH:16][CH:15]=2)[S:30][CH:31]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2938102-Amino-4-methylthiophene-3-carboxamideHCID 447696352-(4-(3-(Piperidin-1-yl)propoxy)phenyl)acetic acid

Product 1

HCID 596366764-Methyl-2-(2-(4-(3-(piperidin-1-yl)propoxy)phenyl)acetamido)thiophene-3-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a stirring mixture of 2-(4-(3-(piperidin-1-yl)propoxy)phenyl)acetic acid (800 mg) in DMF/DCM (6 mL, 1:1) was added triethylamine (1.2 mL), DMAP (180 mg), 2-amino-4-methylthiophene-3-carboxamide (440 mg), and EDCI (1.1 g). The reaction mixture was stirred at rt overnight, quenched with saturated NaHCO3 solution and extracted with EtOAc. The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified via preparative HPLC to give 4-methyl-2-(2-(4-(3-(piperidin-1-yl)propoxy)phenyl)acetamido)thiophene-3-carboxamide. Method[7], MS (ESI) 416.2 [M+H], Retention time=2.254 min.

Workup

  1. customquenched with saturated NaHCO3 solution
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified via preparative HPLC

Sources & evidence

ORD record
ord-46e8287aa9284f33b96d6a694ee4c651
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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