Hydrochloric Acid → HCID 71281241, compound

HRID 570304Notes

Reaction equation

HRID 570304 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]([CH2:25][N:26](C)C(=O)OC(C)(C)C)[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>C(#N)C.O1CCOCC1.O>[NH2:26][CH2:25][C:23]1[O:22][N:21]=[C:20]([C:15]2[CH:16]=[CH:17][C:18]([CH3:19])=[C:13]([NH:12][C:10]([C:3]3[N:4]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]4=[N:1][CH:2]=3)=[O:11])[CH:14]=2)[N:24]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 71282310HCID 71282310, compound

Product 1

HCID 71281241HCID 71281241, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirring suspension of tert-butyl (3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)methyl(methyl)carbamate (F54) (90 mg, 0.195 mmol) in acetonitrile (1 mL) was added 4N HCl in dioxane (1 mL) and water (0.5 mL). The reaction mixture was stirred at room temperature for 45 minutes. Then, the solvent was concentrated and the crude product was dried under high vacuum. The crude product N-(5-(5-(aminomethyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (26) was used in the next step without further purification. 1H NMR (400 MHz, d6-DMSO) δ 10.04 (s, 1 H), 9.46-9.44 (m, 1 H), 8.74 (s, 2 H), 8.63 (s, 1 H), 8.15 (d, J=2.0 Hz, 1 H), 7.86-7.80 (m, 2 H), 7.59-7.54 (m, 1 H), 7.55 (d, J=8.4 Hz, 1 H), 7.23-7.20 (m, 1 H), 4.62 (s, 2 H), 2.39 (s, 3 H). MS m/z 349.4 (M+1)+.

Workup

  1. concentrationThen, the solvent was concentrated
  2. dry with materialthe crude product was dried under high vacuum
  3. customThe crude product N-(5-(5-(aminomethyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (26) was used in the next step without further purification

Sources & evidence

ORD record
ord-c22ff611657e448fab6b113a9ec81037
Source dataset
uspto-grants-2015_05
Patent number
US09023839B2

Reaction notes

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