Trifluoroacetic acid → HCID 86726704, compound

HRID 1499458Notes

Reaction equation

HRID 1499458 reaction equation
C(OC([NH:8][C:9]1[S:13][C:12]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])=[N:11][C:10]=1[C:22]([NH:24][C:25]1[C:26]([N:35]2[CH2:40][CH2:39][CH2:38][C@H:37]([NH:41]C(=O)OC(C)(C)C)[CH2:36]2)=[C:27]2[CH2:33][CH2:32][C:31](=[O:34])[C:28]2=[N:29][CH:30]=1)=[O:23])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[S:13][C:12]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])=[N:11][C:10]=1[C:22]([NH:24][C:25]1[C:26]([N:35]2[CH2:40][CH2:39][CH2:38][C@H:37]([NH2:41])[CH2:36]2)=[C:27]2[CH2:33][CH2:32][C:31](=[O:34])[C:28]2=[N:29][CH:30]=1)=[O:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86726700HCID 86726700, compound

Product 1

HCID 86726704HCID 86726704, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl {(3S)-1-[3-({[5-[(tert-butoxycarbonyl)amino]-2-(2,6-difluorophenyl)-1,3-thiazol-4-yl]carbonyl}amino)-7-oxo-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl]piperidin-3-yl}carbamate (2.0 mg, 0.0029 mmol) in DCM (0.009 mL) was treated with TFA (0.01 mL, 0.1 mmol). The reaction mixture was stirred at room temperature for 1 h, concentrated and then diluted with MeOH and neutralized with NH4OH. After filtration, the crude was purified by preparative LC-MS (XBridge™ preparative C18 5 μm 30×10 mm OBD™ column, flow rate 60 mL/min., eluting with a gradient of MeCN and water with 0.15% NH4OH) to give the title compound as white powder (1.3 mg, 92%). LCMS calc. for C23H23F2N6O2S (M+H)+: m/z=485.2. Found: 485.1.

Workup

  1. concentrationconcentrated
  2. additiondiluted with MeOH and neutralized with NH4OH
  3. filtrationAfter filtration
  4. customthe crude was purified by preparative LC-MS (XBridge™ preparative C18 5 μm 30×10 mm OBD™ column, flow rate 60 mL/min.
  5. washeluting with a gradient of MeCN and water with 0.15% NH4OH)

Sources & evidence

ORD record
ord-aa08e4c4996b414fb87a1a59216bed05
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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