Triethylamine → (R)-benzyl 4-(dimethylamino)-3-(5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)thiophene-2-sulfonamido)butanoate

HRID 1958731Notes

Reaction equation

HRID 1958731 reaction equation
[NH2:1][C@@H:2]([CH2:14][N:15]([CH3:17])[CH3:16])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].C(N(CC)CC)C.[CH3:25][N:26]1[C:30]([C:31]2[S:35][C:34]([S:36](Cl)(=[O:38])=[O:37])=[CH:33][CH:32]=2)=[CH:29][C:28]([C:40]([F:43])([F:42])[F:41])=[N:27]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:17][N:15]([CH3:16])[CH2:14][C@H:2]([NH:1][S:36]([C:34]1[S:35][C:31]([C:30]2[N:26]([CH3:25])[N:27]=[C:28]([C:40]([F:41])([F:42])[F:43])[CH:29]=2)=[CH:32][CH:33]=1)(=[O:37])=[O:38])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27756735-[1-Methyl-3-(trifluoromethyl)-1h-pyrazol-5-yl]thiophene-2-sulfonyl chlorideHCID 46223508(R)-benzyl 3-amino-4-(dimethylamino)butanoate

Product 1

HCID 86641225(R)-benzyl 4-(dimethylamino)-3-(5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)thiophene-2-sulfonamido)butanoateYield 57%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-benzyl 3-amino-4-(dimethylamino)butanoate (27 mg, 0.086 mmol), triethylamine (50 μL, 0.36 mmol) and DMAP (1 mg, 0.008 mmol) in anhydrous CH2Cl2 (1 mL) was added 5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)thiophene-2-sulfonyl chloride (82 mg, 0.25 mmol). The solution was stirred overnight at room temperature. The solvents were removed in vacuo and the residue was purified by preparatory HPLC. The residue was dissolved into CH2Cl2 (50 mL) and washed with 0.1 N NaOH (5 mL), dried over MgSO4 and concentrated to give the title compound as a white solid (26 mg, 57%). MS ESI 531.2 [M+H]+, calcd for [C22H25F3N4O4S2+H]+ 531.13.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was purified by preparatory HPLC
  3. dissolutionThe residue was dissolved into CH2Cl2 (50 mL)
  4. washwashed with 0.1 N NaOH (5 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ae4b3133b406488c9935adbbcc96f5e4
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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