Hydrochloric Acid → HCID 71280395, compound

HRID 1497905Notes

Reaction equation

HRID 1497905 reaction equation
[N:1]1[CH:2]=[C:3]([C:10]([NH:12][C:13]2[CH:14]=[C:15]([C:20]3[N:24]=[C:23]([C:25]4([NH:28]C(=O)OC(C)(C)C)[CH2:27][CH2:26]4)[O:22][N:21]=3)[CH:16]=[CH:17][C:18]=2[CH3:19])=[O:11])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.Cl>O1CCOCC1>[NH2:28][C:25]1([C:23]2[O:22][N:21]=[C:20]([C:15]3[CH:16]=[CH:17][C:18]([CH3:19])=[C:13]([NH:12][C:10]([C:3]4[N:4]5[CH:9]=[CH:8][CH:7]=[CH:6][C:5]5=[N:1][CH:2]=4)=[O:11])[CH:14]=3)[N:24]=2)[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71280205HCID 71280205, compound

Product 1

HCID 71280395HCID 71280395, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a vial was added tert-butyl (1-(3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)cyclopropyl)carbamate (F67) (275 mg, 0.6 mmol) and 4N HCl in 1,4-dioxane (3 mL). The reaction was stirred for 30 minutes. The solvent was concentrated and placed under high vacuum. The solid was taken in water/acetonitrile and the pH was adjusted to neutral with an aqueous solution of ammonium carbonate and lyophilized to afford N-(5-(5-(1-aminocyclopropyl)-1,2,4-oxadiazol-3-yl)-2methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (156). MS m/z 375.1 (M+1)+.

Workup

  1. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-d7b846ad773647bcaaafed85ff696cd3
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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