Trifluoroacetic acid → HCID 71164923, compound

HRID 2173076Notes

Reaction equation

HRID 2173076 reaction equation
C(OC([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[N:21]=[C:20]([C:22]2[S:30][C:25]3=[CH:26][N:27]=[CH:28][CH:29]=[C:24]3[CH:23]=2)[C:19]2[C:31](=[O:41])[N:32](C(OC(C)(C)C)=O)[CH2:33][C:18]=2[C:17]=1[F:42])=O)(C)(C)C.[C:43]([OH:49])([C:45]([F:48])([F:47])[F:46])=[O:44]>C(Cl)Cl>[C:43]([OH:49])([C:45]([F:48])([F:47])[F:46])=[O:44].[NH2:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[N:21]=[C:20]([C:22]2[S:30][C:25]3=[CH:26][N:27]=[CH:28][CH:29]=[C:24]3[CH:23]=2)[C:19]2[C:31](=[O:41])[NH:32][CH2:33][C:18]=2[C:17]=1[F:42]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71164941HCID 71164941, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 71164923HCID 71164923, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 6-(((1R,2S)-2-((tert-butoxycarbonyl)amino)cyclohexyl)amino)-7-fluoro-3-oxo-4-(thieno[2,3-c]pyridin-2-yl)-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (135 mg, 226 mmol) in DCM (3 mL) was added TFA in DCM (1:1, 10 mL). The reaction mixture was stirred at room temperature for 1 hour. After removal of the solvent, the resulting crude material was reconstituted in MeOH/DMF/DCM (10.0 mL) and was purified via preparative mass trigger LCMS, eluting with a gradient of 10-25% ACN (0.035% TFA) and H2O (0.05% TFA). The collected fractions were combined and the solvent was stripped to dryness via rotary evaporation to give a TFA salt of the title compound (76 mg, 48% two steps). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.48-2.06 (m, 8H), 3.83 (br s, 1H), 4.34 (d, J=3.28 Hz, 1H), 4.57 (s, 2H), 7.35 (d, J=6.06 Hz, 1H), 7.88 (br s, 2H), 8.20 (d, J=5.81 Hz, 1H), 8.58 (d, J=5.81 Hz, 1H), 8.81 (s, 1H), 9.47 (s, 1H), 9.61 (s, 1H). ESI-MS m/z [M+H]+ calc'd for C20H20FN5OS, 398. found, 398.

Workup

  1. customAfter removal of the solvent
  2. customwas purified via preparative mass trigger LCMS
  3. washeluting with a gradient of 10-25% ACN (0.035% TFA) and H2O (0.05% TFA)
  4. customthe solvent was stripped to dryness via rotary evaporation

Sources & evidence

ORD record
ord-e8b37cd827d34e799bdf22a91b2dcff9
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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