Hydrochloric Acid → HCID 58138817, compound

HRID 1677700Notes

Reaction equation

HRID 1677700 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16]([C:18]2[C:19]3[CH:20]=[N:21][N:22]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[C:23]=3[CH:24]=[CH:25][CH:26]=2)=[O:17])=[CH:10][N:9]=1)(C)(C)C.C(OC(=O)NC1C=CC(CN)=CN=1)(C)(C)C.Cl.O1CCOCC1>>[NH2:7][C:8]1[N:9]=[CH:10][C:11]([CH2:14][NH:15][C:16]([C:18]2[C:19]3[CH:20]=[N:21][N:22]([C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=4)[C:23]=3[CH:24]=[CH:25][CH:26]=2)=[O:17])=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 42553118tert-Butyl hydrogen [5-(aminomethyl)pyridin-2-yl]carbonimidateHCID 58138908HCID 58138908, compound

Product 1

HCID 58138817HCID 58138817, compound

Procedure

[5-({[1-(4-Fluoro-phenyl)-1H-indazole-4-carbonyl]-amino}-methyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (0.200 g, 0.433 mmol) synthesized as described in Example 4, via the acid chloride and tert-butyl[5-(aminomethyl)pyridine-2-yl]carbamate) was treated with a solution of 4 N HCl in dioxane (5 mL, 20 mmol) and stirred for 6 hours at room temperature. A solid was obtained by filtration, and partitioned between saturated aqueous NaHCO3 (10 mL) and ethyl acetate (10 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The resulting solid was triturated with ethyl acetate (1 mL), filtered and air dried to afford the title compound as a white crystalline solid.

Workup

  1. customA solid was obtained by filtration
  2. custompartitioned between saturated aqueous NaHCO3 (10 mL) and ethyl acetate (10 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×10 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting solid was triturated with ethyl acetate (1 mL)
  9. filtrationfiltered
  10. customair dried

Sources & evidence

ORD record
ord-9c82e2d144524380aff52fbdf9cb6b19
Source dataset
uspto-grants-2011_08
Patent number
US08008327B2

Reaction notes

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