Trifluoroacetic acid → HCID 86726653, compound

HRID 1499396Notes

Reaction equation

HRID 1499396 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[CH:26]=[N:27][C:28]2[C:33]([C:34]=1[N:35]1[CH2:40][CH2:39][CH2:38][C@H:37]([NH:41]C(=O)OC(C)(C)C)[CH2:36]1)=[CH:32][CH:31]=[CH:30][CH:29]=2)=[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[CH:26]=[N:27][C:28]2[C:33]([C:34]=1[N:35]1[CH2:40][CH2:39][CH2:38][C@H:37]([NH2:41])[CH2:36]1)=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86726652HCID 86726652, compound

Product 1

HCID 86726653HCID 86726653, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl {(3S)-1-[3-({[5-[(tert-butoxycarbonyl)amino]-2-(2,6-difluorophenyl)-1,3-thiazol-4-yl]carbonyl}amino)quinolin-4-yl]piperidin-3-yl}carbamate (115.8 mg, 0.17 mmol) in DCM (2.0 mL) was added TFA (2.0 mL). The mixture was stirred at room temperature for 30 min., and then concentrated under reduced pressure. The resulting residue was purified using RP-HPLC (XBridge™ C18 column, eluting with a gradient of MeCN/water containing 0.15% NH4OH, at flow rate of 30 mL/min.) to afford the title compound as a white solid (20.5 mg, 25%). LCMS calc. for C24H23F2N6OS (M+H)+: m/z=481.2. found 481.2.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting residue was purified
  3. washeluting with a gradient of MeCN/water containing 0.15% NH4OH, at flow rate of 30 mL/min.)

Sources & evidence

ORD record
ord-1aeb3f376c4c496b9ee4a03580ec11cb
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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