Trifluoroacetic acid → N-(5-(5-(3-(3-hydroxypropylidene)cyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 1497917Notes

Reaction equation

HRID 1497917 reaction equation
[CH:1]1([C:4]2(O)[CH2:7][CH:6]([C:8]3[O:12][N:11]=[C:10]([C:13]4[CH:14]=[CH:15][C:16]([CH3:31])=[C:17]([NH:19][C:20]([C:22]5[N:26]6[CH:27]=[CH:28][CH:29]=[CH:30][C:25]6=[N:24][CH:23]=5)=[O:21])[CH:18]=4)[N:9]=3)[CH2:5]2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=[O:36]>>[OH:36][CH2:2][CH2:3][CH:1]=[C:4]1[CH2:5][CH:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[CH:15][C:16]([CH3:31])=[C:17]([NH:19][C:20]([C:22]4[N:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]5=[N:24][CH:23]=4)=[O:21])[CH:18]=3)[N:9]=2)[CH2:7]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71280497N-(5-(5-(3-cyclopropyl-3-hydroxycyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 71280588N-(5-(5-(3-(3-hydroxypropylidene)cyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

Procedure

A stirring solution of N-(5-(5-(3-cyclopropyl-3-hydroxycyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F113) (130 mg, 0.303 mmol) in trifluoroacetic acid (1 mL) was stirred at room temperature for 1.5 hours. The solvent was concentrated and dried under high vacuum. The crude product was taken in MeOH (1 mL) and a saturated solution of sodium bicarbonate (0.2 mL). The reaction mixture was stirred for 15 minutes. The crude product was extracted with ethyl acetate. The organic phase was washed with water and dried over anhydrous sodium sulfate. The solvent was concentrated to obtain the desired product N-(5-(5-(3-(3-hydroxypropylidene)cyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F32). 1H NMR (400 MHz, d6-DMSO) δ 10.04 (s, 1H), 9.48-9.45 (m, 1H), 8.59 (s, 1H), 8.08 (d, J=1.6 Hz, 1H), 7.82 (dd, J=1.6 Hz, 7.6 Hz, 1H), 7.81-7.77 (m, 1H), 7.55-7.52 (m, 1H), 7.49 (d, J=8.0 Hz, 1H), 7.20-7.16 (m, 1H), 5.28-5.23 (m, 1H), 4.50 (s, 1H), 3.98-3.89 (m, 1H), 3.40-3.37 (m, 2H), 3.23-3.14 (m, 2H), 3.09-3.03 (m, 2H), 2.36 (s, 3H), 2.08-2.02 (m, 2H). MS m/z 430.47 (M+1)+.

Workup

  1. concentrationThe solvent was concentrated
  2. customdried under high vacuum
  3. extractionThe crude product was extracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-e55c4ecb5a2145b8b41c8ed0b25240a0
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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