Hydrochloric Acid → HCID 71280200, compound

HRID 246712Notes

Reaction equation

HRID 246712 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([CH2:27][NH:28]C(=O)OC(C)(C)C)[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:36]>O1CCOCC1>[ClH:36].[NH2:28][CH2:27][C:24]1([NH:23][C:21]([C:20]2[C:14]3[C:15](=[N:16][CH:17]=[C:12]([C:6]4[C:5]5[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=5)[N:8]([CH3:11])[N:7]=4)[N:13]=3)[NH:18][CH:19]=2)=[O:22])[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71288483HCID 71288483, compound

Product 1

HCID 71280200HCID 71280200, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl (1-(2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)cyclopropyl)methylcarbamate (95 mg, 0.20 mmol) was dissolved in 20 mL of a saturated solution of HCl (g) in dioxane and the solution was stirred at room temperature for 3 hours. The solvent was evaporated at 40° C. under reduced pressure and the residue was triturated with ethyl acetate (10 mL) then decanted and dried to give N-(1-(aminomethyl)cyclopropyl)-2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide hydrochloride (13 mg, 15.8%) as a pale yellow solid. MS: (M+H)+=380.1; 1H NMR (300 MHz, CD3OD): δ 9.18 (s, 1H), 8.43-8.41 (m, 2H), 7.45 (d, 1H, J=9.3 Hz), 7.19 (s, 1H), 4.17 (s, 3H), 3.32 (s, 2H), 1.25 (s, 4H).

Workup

  1. customThe solvent was evaporated at 40° C. under reduced pressure
  2. customthe residue was triturated with ethyl acetate (10 mL)
  3. customthen decanted
  4. customdried

Sources & evidence

ORD record
ord-35a2f61c391146c0bdc94e97ba4a9f66
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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