Hydrochloric Acid → HCID 71281044, compound

HRID 570299Notes

Reaction equation

HRID 570299 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]([CH:25]4[CH2:28][N:27](C(OC(C)(C)C)=O)[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.CC#N>[NH:27]1[CH2:26][CH:25]([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)[CH2:28]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71281109HCID 71281109, compound

Product 1

HCID 71281044HCID 71281044, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

To a vial was added tert-butyl 3-(3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate (F39) (145 mg, 0.3 mmol) and 4N HCl in 1,4-dioxane (2 mL) and CH3CN (1 mL). The reaction was stirred for 45 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-(azetidin-3-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (21) which was used directly in the next step. 1H NMR (400 MHz, d6-DMSO) δ 10.85 (s, 1 H), 9.66-9.64 (m, 1 H), 9.42 (bs, 1 H), 9.28 (s, 1 H), 8.10-8.08 (m, 2 H), 8.02-7.98 (m, 1 H), 7.89-7.87 (m, 1H), 7.59-7.53 (m, 2 H), 4.53-4.47 (m, 1 H), 4.36-4.29 (m, 4 H), 2.40 (s, 3 H). MS m/z 375.1 (M+1)+.

Workup

  1. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-08d731a925824f11acb6e2223c1b1388
Source dataset
uspto-grants-2015_05
Patent number
US09023839B2

Reaction notes

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