Hydrochloric Acid → HCID 58010243, compound

HRID 2204606Notes

Reaction equation

HRID 2204606 reaction equation
C(OC([N:8]([C:29]1[N:30]=[C:31]2[CH:37]=[CH:36][N:35]([S:38]([C:41]3[CH:47]=[CH:46][C:44]([CH3:45])=[CH:43][CH:42]=3)(=[O:40])=[O:39])[C:32]2=[N:33][CH:34]=1)[CH2:9][C:10]([CH:12]1[CH:17]([CH3:18])[CH2:16][CH2:15][N:14]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:13]1)=[O:11])=O)(C)(C)C.Cl>>[CH3:18][CH:17]1[CH2:16][CH2:15][N:14]([C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])[CH2:13][CH:12]1[C:10](=[O:11])[CH2:9][NH:8][C:29]1[N:30]=[C:31]2[CH:37]=[CH:36][N:35]([S:38]([C:41]3[CH:47]=[CH:46][C:44]([CH3:45])=[CH:43][CH:42]=3)(=[O:40])=[O:39])[C:32]2=[N:33][CH:34]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 58010260HCID 58010260, compound

Product 1

HCID 58010243HCID 58010243, compoundYield 100%

Procedure

Benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-methylpiperidine-1-carboxylate (1.45 g, 2.2 mmol) was stirred in HCl (4 N in 1,4-dioxane, 0.55 mL, 2.2 mmol) at ambient temperature for about 90 min. The solvent was removed under reduced pressure and the residue was neutralized with saturated aqueous NaHCO3. The aqueous phase was extracted with EtOAc (2×20 mL) and the combined organic extracts were washed with brine (16 mL), dried over anhydrous MgSO4, filtered, and concentrated to yield benzyl 4-methyl-3-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)acetyl)piperidine-1-carboxylate (1.23 g, 100%) as a brown amorphous solid: LC/MS (Table 2, Method a) Rt=2.74 min; MS m/z: 562 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionThe aqueous phase was extracted with EtOAc (2×20 mL)
  3. washthe combined organic extracts were washed with brine (16 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4804f5d7bd7c44e192ba912559e52e13
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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