Trifluoroacetic acid → HCID 178527558, compound

HRID 2406224Notes

Reaction equation

HRID 2406224 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C@@H:28]([CH2:37][S:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH2:29][CH2:30][N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)=[C:23]([S:45]([C:48]([F:51])([F:50])[F:49])(=[O:47])=[O:46])[CH:22]=3)(=[O:20])=[O:19])=[N:15][N:16]=[C:10]2[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[N:31]1([CH2:30][CH2:29][C@@H:28]([NH:27][C:24]2[CH:25]=[CH:26][C:21]([S:18]([NH:17][C:14]3[N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH:10]4[NH:16][N:15]=3)(=[O:19])=[O:20])=[CH:22][C:23]=2[S:45]([C:48]([F:50])([F:51])[F:49])(=[O:47])=[O:46])[CH2:37][S:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67980827HCID 67980827, compound

Product 1

HCID 178527558HCID 178527558, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[4-((R)-3-morpholin-4-yl-1-phenylsulfanylmethyl-propylamino)-3-trifluoromethanesulfonyl-benzenesulfonylamino]-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazine-7-carboxylic acid tert-butyl ester (130 mg, 0.168 mmol) in dichloromethane (3 mL) under nitrogen was added trifluoroacetic acid (0.323 mL, 4.19 mmol), and the reaction was stirred for 2.5 hours. The reaction mixture was then concentrated and diluted with water and CH2Cl2. It was then basified to pH approximately 8 with saturated Na2CO3. The organics were extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the title compound (112 mg, 99% yield). MS [m/z; (M+1)+]: 676.5

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additiondiluted with water and CH2Cl2
  3. extractionThe organics were extracted three times with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b32324ff4cf491f99b345b39ca784e8
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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