Hydrochloric Acid → HCID 71281006, compound

HRID 570357Notes

Reaction equation

HRID 570357 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]([S:29]([NH:32]C(=O)OC(C)(C)C)(=[O:31])=[O:30])[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>CC#N>[CH3:19][C:18]1[CH:17]=[CH:16][C:15]([C:20]2[N:24]=[C:23]([CH:25]3[CH2:28][N:27]([S:29](=[O:31])(=[O:30])[NH2:32])[CH2:26]3)[O:22][N:21]=2)=[CH:14][C:13]=1[NH:12][C:10]([C:3]1[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:1][CH:2]=1)=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71281141HCID 71281141, compound

Product 1

HCID 71281006HCID 71281006, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirring solution of tert-butyl 3-(3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)azetidin-1-ylsulfonylcarbamate (128) (25 mg, 0.0452 mmol) in CH3CN (0.5 mL) was added HCl (4N in dioxane, 1 mL). The reaction was stirred for 30 minutes. The solvent was concentrated and the crude was purified by preparative HPLC to give N-(2-methyl-5-(5-(1-sulfamoylazetidin-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide (F23). 1H NMR (400 MHz, d6-DMSO) δ 10.14 (s, 1H), 9.51-9.48 (m, 1H), 8.67 (s, 1H), 8.11 (d, J=1.6 Hz, 1H), 7.87-7.84 (m, 2H), 7.66-7.61 (m, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.29-7.25 (m, 1H), 7.13 (s, 2H), 4.24-4.18 (m, 1H), 4.16-4.12 (m, 2H), 4.05-4.01 (m, 2H), 2.37 (s, 3H). MS m/z 454.59 (M+1)+.

Workup

  1. concentrationThe solvent was concentrated
  2. customthe crude was purified by preparative HPLC

Sources & evidence

ORD record
ord-f3ff8ed7cc98425c95449300ef0caec7
Source dataset
uspto-grants-2015_05
Patent number
US09023839B2

Reaction notes

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