Hydrochloric Acid → N-(4-(3-amino-3-methylpiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methoxyacetamide hydrochloride

HRID 1034722Notes

Reaction equation

HRID 1034722 reaction equation
[NH2:1][C:2]1([CH3:24])[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[C:13]([Br:14])=[CH:12][N:11]=[C:10]3[NH:15][CH:16]=[C:17]([NH:18][C:19](=[O:23])[CH2:20][O:21][CH3:22])[C:9]=23)[CH2:3]1.[ClH:25]>CO.O1CCOCC1>[ClH:25].[NH2:1][C:2]1([CH3:24])[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[C:13]([Br:14])=[CH:12][N:11]=[C:10]3[NH:15][CH:16]=[C:17]([NH:18][C:19](=[O:23])[CH2:20][O:21][CH3:22])[C:9]=23)[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58195557N-(4-(3-Amino-3-methylpiperidin-1-yl)-5-bromo-1H-pyrrolo [2,3-b]pyridin-3-yl)-2-methoxyacetamide

Product 1

HCID 60205374N-(4-(3-amino-3-methylpiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methoxyacetamide hydrochlorideYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

N-(4-(3-Amino-3-methylpiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methoxyacetamide (65 mg, 0.16 mmol) was dissolved in a minimal amount of methanol and then added to a stirred solution of 4N HCl in dioxane. The resulting solid was filtered and dried under high vacuum to yield N-(4-(3-amino-3-methylpiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methoxyacetamide hydrochloride (36 mg, 55% yield) as a solid. 1H NMR (400 MHz, (CD3)2SO)S11.90 (d, 1H), 9.38 (s, 1H), 8.26 (s, 1H), 8.24 (br s, 2H), 6.30 (br s, 3H), 4.11 (q, 2H), 3.43 (s, 3H), 3.30-3.21 (m, 1H), 3.20-3.05 (m, 3H), 2.00-1.90 (m, 1H), 1.86-1.75 (m, 3H), 1.46 (s, 3H); LCMS (APCI+) m/z 379, 396 (M)+, Retention time=1.90 minutes (Method 1).

Workup

  1. filtrationThe resulting solid was filtered
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-5418f6c77c62476c901ef26284277ab4
Source dataset
uspto-grants-2013_10
Patent number
US08545897B2

Reaction notes

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