Methyl 2-(2,2,2-trifluoroacetamido)imidazo[1,2-a]pyridine-6-carboxylate → HCID 59233078, compound

HRID 1925099Notes

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([C:14](OC)=[O:15])=[CH:10][N:9]2[CH:18]=1)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:20][C:2]([F:1])([F:19])[C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][N:9]2[CH:18]=1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of compound 1B (470 mg, 1.64 mmol) in anhydrous THF (20 mL) were portion wise added lithium aluminum hydride (155 mg, 4.09 mmol) at 0° C. After being stirred for 1 h at 0° C., the reaction was quenched with 0.16 mL of water, followed by 0.16 mL of 15% NaOH and 0.48 mL of water. The heterogenous reaction mixture was stirred for 0.5 h at room temperature and then filtered through celite. Residue was washed with THF. Filtrate and washings were concentrated and the crude residue was purified by column chromatography to furnish compound 1C (220 mg, 52%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.41 (s, 1H), 8.52 (s, 1H), 8.21 (s, 1H), 7.47 (d, J=9.2 Hz, 1H), 7.25 (d, J=9.6 Hz, 1H), 5.36 (t, J=5.6 Hz, 1H) 4.48 (d, J=5.6 Hz, 2 H) ESI-MS:m/z 260.2 (M+H)+.

Workup

customat 0° C
customthe reaction was quenched with 0.16 mL of water
stirringThe heterogenous reaction mixture was stirred for 0.5 h at room temperature
filtrationfiltered through celite
washResidue was washed with THF
concentrationFiltrate and washings were concentrated
customthe crude residue was purified by column chromatography

Sources & evidence

ORD record: ord-1128f5f935b3485887be77da31950d7f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178534B2

Reaction notes

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