Triethylamine → HCID 24967418, compound

HRID 1162740Notes

Reaction equation

HRID 1162740 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[C:14]2[CH2:38][CH2:37][CH2:36][CH2:35][C:15]=2[S:16][C:17]=1[NH:18][C:19](=[O:34])[CH2:20][N:21]1[C:29]2[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=2[C:23]([C:30]([F:33])([F:32])[F:31])=[N:22]1)=[O:12])(C)(C)C.C(N(CC)CC)C.[CH3:47][S:48](Cl)(=[O:50])=[O:49]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:47][S:48]([NH:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[C:14]2[CH2:38][CH2:37][CH2:36][CH2:35][C:15]=2[S:16][C:17]=1[NH:18][C:19](=[O:34])[CH2:20][N:21]1[C:29]2[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=2[C:23]([C:30]([F:32])([F:33])[F:31])=[N:22]1)=[O:12])(=[O:50])=[O:49]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59520457HCID 59520457, compound

Product 1

HCID 24967418HCID 24967418, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

[2-({2-[2-(3-Trifluoromethyl-4,5,6,7-tetrahydroindazol-1-yl)-acetylamino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonyl}-amino)-ethyl]-carbamic acid tert-butyl ester was dissolved in a solution of DCM (1 mL) and TFA (1 mL) and stirred at RT for 1 h, before concentration in vacuo. The resulting colourless oil was redissolved in DCM (1 mL) and triethylamine (7.70 μL, 0.055 mmol) added, followed by methanesulfonyl chloride (2.20 μL, 0.028 mmol). The resulting mixture was stirred at RT overnight. The sample was concentrated in vacuo and the residue obtained purified by preparative reverse phase HPLC to yield the title compound as a white solid (4 mg, 0.007 mmol, 25%).

Workup

  1. stirringThe resulting mixture was stirred at RT overnight
  2. concentrationThe sample was concentrated in vacuo
  3. customthe residue obtained
  4. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-b06d6d2319544bc5a6c1bdfda38d2d49
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

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