Hydrochloric Acid → HCID 68757731, compound

HRID 387609Notes

Reaction equation

HRID 387609 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([C@@H:28]2[CH2:32][CH2:31][CH2:30][N:29]2C(OC(C)(C)C)=O)[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[C:23]([CH3:24])=[CH:22][N:21]=[C:20]4[NH:25][N:26]=[CH:27][C:19]=34)[CH2:14][CH2:13]2)=[O:11])=[CH:5][CH:4]=1>O1CCOCC1>[ClH:2].[ClH:1].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([C@@H:28]2[CH2:32][CH2:31][CH2:30][NH:29]2)[C:10]([N:12]2[CH2:13][CH2:14][N:15]([C:18]3[C:23]([CH3:24])=[CH:22][N:21]=[C:20]4[NH:25][N:26]=[CH:27][C:19]=34)[CH2:16][CH2:17]2)=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68759055HCID 68759055, compound

Product 1

HCID 68757731HCID 68757731, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4N HCl in dioxane (5 mL) was added to (S)-tert-butyl 2-((S)-1-(4-chlorophenyl)-2-(4-(5-methyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazin-1-yl)-2-oxoethyl)pyrrolidine-1-carboxylate (68 mg, 0.13 mmol), and the mixture was stirred at room temperature. After 30 minutes, the solvent was removed under reduced pressure, and the resulting residue was triturated with ether. The solid material was filtered, washed with additional ether (2×2 mL) and dried under high vacuum for 24 hours to provide (S)-2-(4-chlorophenyl)-1-(4-(5-methyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazin-1-yl)-2-((S)-pyrrolidin-2-yl)ethanone dihydrochloride (62 mg, 0.12 mmol, 96% yield) as a solid. LCMS (APCI+) m/z 439.1 (M+H)+. NMR (400 Hz, DMSO-d6) δ 9.98 (brs, 1H), 9.06 (s, 1H), 8.23 (s, 1H), 7.49 (d, 2H), 7.43 (d, 2H), 4.56 (d, 1H), 4.03-3.96 (m, 2H), 3.93-3.87 (m, 3H), 3.71-3.65 (m, 1H), 3.64-3.57 (m, 2H), 3.50-3.46 (m, 1H), 3.19-3.13 (m, 2H), 2.31 (s, 3H), 1.97-1.89 (m, 1H), 1.78-1.70 (m, 1H), 1.63-1.52 (m, 2H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe resulting residue was triturated with ether
  3. filtrationThe solid material was filtered
  4. washwashed with additional ether (2×2 mL)
  5. customdried under high vacuum for 24 hours

Sources & evidence

ORD record
ord-7fba96e69df04ae49e8af6de9e80ff33
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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