Hydrochloric Acid → 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(4-methylpiperidin-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide hydrochloride

HRID 246585Notes

Reaction equation

HRID 246585 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21]([NH:23][C:24]5([CH3:37])[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]5)=[O:22])=[CH:19][NH:18][C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.[ClH:38]>O1CCOCC1>[ClH:38].[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21]([NH:23][C:24]5([CH3:37])[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]5)=[O:22])=[CH:19][NH:18][C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71280124tert-butyl 4-(2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)-4-methylpiperidine-1-carboxylate

Product 1

HCID 712801422-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(4-methylpiperidin-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide hydrochlorideYield 33.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-(2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)-4-methylpiperidine-1-carboxylate (100 mg, 0.20 mmol) was dissolved in 30 mL of a saturated solution of HCl (g) in dioxane and the solution was stirred at room temperature for 16 hours. The reaction mixture was filtered, washed with dichloromethane (20 mL), diethyl ether (30 mL) and dried to give 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(4-methylpiperidin-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide hydrochloride (29 mg, 33.2%) as a white solid. MS: (M+H)+=408; 1H NMR (300 MHz, DMSO): δ 9.16 (s, 1H), 8.57-8.41 (m, 4H), 7.92 (s, 1H), 7.75 (d, 1H, J=10.5 Hz), 7.32-7.26 (m, 1H), 6.98-6.93 (m, 1H), 5.75 (d, 2H, J=6.9 Hz), 4.19 (s, 3H), 3.16 (brs, 5H), 1.96 (brs, 3H), 1.61 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with dichloromethane (20 mL), diethyl ether (30 mL)
  3. customdried

Sources & evidence

ORD record
ord-660016705e9f4150a39765216f9aa08f
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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