Hydrochloric Acid → HCID 67976200, compound

HRID 1502268Notes

Reaction equation

HRID 1502268 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][N:5](C2CCCCO2)[C:6]=1[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([NH:17][C:18]([CH:20]3[CH2:22][CH2:21]3)=[O:19])[N:13]=[CH:14]2)=[CH:9][CH:8]=1.CO.[ClH:31]>O1CCOCC1>[ClH:31].[CH3:1][C:2]1[CH:3]=[N:4][NH:5][C:6]=1[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([NH:17][C:18]([CH:20]3[CH2:22][CH2:21]3)=[O:19])[N:13]=[CH:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 71115127HCID 71115127, compound

Product 1

HCID 67976200HCID 67976200, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of N-(7-(4-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)isoquinolin-3-yl)cyclopropanecarboxamide (43 mg, 0.11 mmol) in methanol (3 mL, 70 mmol) was added 4.0 M of hydrogen chloride in 1,4-dioxane (0.30 mL). The reaction mixture was stirred at 40° C. for 1 hour and then evaporated in vacuo. The residue was triturated with 0.5 mL N,N-dimethylformamide, and the resulting light yellow precipitate was collected, rinsed with ethyl acetate, and dried under vacuum to yield 17.3 mg (46%) of N-(7-(4-methyl-1H-pyrazol-5-yl)isoquinolin-3-yl)cyclopropanecarboxamide hydrochloride. LCMS (ESI): RT (Min)=3.816, M+H=293.0, method=E; 1H NMR (400 MHz, DMSO-d6) δ 10.96 (s, 1H), 9.22 (s, 1H), 8.44 (s, 1H), 8.27 (s, 1H), 8.06 (d, J=8.8 Hz, 1H), 7.92 (d, J=8.7 Hz, 1H), 7.63 (s, 1H), 2.31 (s, 3H), 2.14-2.01 (m, 1H), 0.93-0.76 (m, 4H).

Workup

  1. customevaporated in vacuo
  2. customThe residue was triturated with 0.5 mL N,N-dimethylformamide
  3. customthe resulting light yellow precipitate was collected
  4. washrinsed with ethyl acetate
  5. customdried under vacuum

Sources & evidence

ORD record
ord-5d226445b791409b8426d8b7974f1e3c
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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