Hydrochloric Acid → HCID 86726702, compound

HRID 1499456Notes

Reaction equation

HRID 1499456 reaction equation
C[Mg]Br.[C:4]([O:8][C:9]([NH:11][C:12]1[S:16][C:15]([C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])=[N:14][C:13]=1[C:25]([NH:27][C:28]1[C:29]([N:38]2[CH2:43][CH2:42][CH2:41][C@H:40]([NH:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[CH2:39]2)=[C:30]2[CH2:36][CH2:35][C:34](=[O:37])[C:31]2=[N:32][CH:33]=1)=[O:26])=[O:10])([CH3:7])([CH3:6])[CH3:5].[CH3:52]COC(C)=O.Cl>C1COCC1>[C:4]([O:8][C:9]([NH:11][C:12]1[S:16][C:15]([C:17]2[C:18]([F:24])=[CH:19][CH:20]=[CH:21][C:22]=2[F:23])=[N:14][C:13]=1[C:25]([NH:27][C:28]1[C:29]([N:38]2[CH2:43][CH2:42][CH2:41][C@H:40]([NH:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[CH2:39]2)=[C:30]2[CH2:36][CH2:35][C:34]([OH:37])([CH3:52])[C:31]2=[N:32][CH:33]=1)=[O:26])=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86726700HCID 86726700, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 86726702HCID 86726702, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methylmagnesium bromide in THF (3.0 M, 5.8 μL, 0.018 mmol) was added to 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 (3.0 mg, 0.0044 mmol) in THF (0.068 mL), which was stirred under N2 and cooled in an ice bath. The reaction mixture was slowly allowed to warmed to room temperature over a period of 1 h. EtOAc was added to the reaction mixture, then 1 M HCl was slowly added to adjust the pH to 7. The aqueous layer was extracted twice with EtOAc. The organic extracts were combined, dried over Na2SO4, then filtered and concentrated under reduced pressure to give the sub-title compound. LCMS calc. for C34H43F2N6O6S (M+H)+: m/z=701.3. Found: 701.1.

Workup

  1. temperaturecooled in an ice bath
  2. extractionThe aqueous layer was extracted twice with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3bb8e138fb442bab73a130283e72b1d
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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