Trifluoroacetic acid → HCID 67980541, compound

HRID 2406248Notes

Reaction equation

HRID 2406248 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][N:17]3[C:20]([NH:23][S:24]([C:27]4[CH:32]=[CH:31][C:30]([NH:33][C@@H:34]([CH2:43][S:44]([C:47]5[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=5)(=O)=O)[CH2:35][CH2:36][N:37]5[CH2:42][CH2:41][O:40][CH2:39][CH2:38]5)=[C:29]([S:53]([C:56]([F:59])([F:58])[F:57])(=[O:55])=[O:54])[CH:28]=4)(=[O:26])=[O:25])=[N:21][N:22]=[C:16]3[CH2:15]2)[CH2:10][CH:9]1[CH3:60])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:60][CH:9]1[CH2:10][CH:11]([N:14]2[CH2:19][CH2:18][N:17]3[C:20]([NH:23][S:24]([C:27]4[CH:32]=[CH:31][C:30]([NH:33][C@@H:34]([CH2:43][S:44][C:47]5[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=5)[CH2:35][CH2:36][N:37]5[CH2:38][CH2:39][O:40][CH2:41][CH2:42]5)=[C:29]([S:53]([C:56]([F:59])([F:57])[F:58])(=[O:55])=[O:54])[CH:28]=4)(=[O:26])=[O:25])=[N:21][N:22]=[C:16]3[CH2:15]2)[CH2:12][CH2:13][NH:8]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86667200HCID 86667200, compound

Product 1

HCID 67980541HCID 67980541, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-4-{3-[4-((R)-3-morpholin-4-yl-1-phenylsulfonylmethylpropyl-amino)-3-trifluoromethanesulfonyl-benzenesulfonylamino]-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl}-piperidine-1-carboxylic acid tert-butyl ester (42 mg, 0.048 mmol) in CH2Cl2 (1 mL) under nitrogen was added trifluoroacetic acid (0.093 mL, 1.203 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 aqueous layer was extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford N-[7-(2-methyl-piperidin-4-yl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazin-3-yl]-4-((R)-3-morpholin-4-yl-1-phenylsulfanylmethyl-propylamino)-3-trifluoromethanesulfonyl-benzenesulfonamide (22 mg, 59% yield). MS [m/z; (M+1)+]: 773.6

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additiondiluted with water and CH2Cl2
  3. extractionThe aqueous layer was 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-d52a271c84234cb68bcc780aecde726e
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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