HCID 71280491、化合物 → HCID 71280656、化合物

HRID 1497925ノート

反応式

HRID 1497925 の反応式
[F:1][C:2]1([F:35])[CH2:5][CH:4]([C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:34])=[C:15]([NH:17][C:18]([C:20]4[N:24]5[CH:25]=[C:26]([CH2:29][CH2:30][C:31](=[O:33])[CH3:32])[CH:27]=[CH:28][C:23]5=[N:22][CH:21]=4)=[O:19])[CH:16]=3)[N:7]=2)[CH2:3]1.[CH3:36][Mg]Br>C1COCC1>[F:35][C:2]1([F:1])[CH2:5][CH:4]([C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:34])=[C:15]([NH:17][C:18]([C:20]4[N:24]5[CH:25]=[C:26]([CH2:29][CH2:30][C:31]([OH:33])([CH3:36])[CH3:32])[CH:27]=[CH:28][C:23]5=[N:22][CH:21]=4)=[O:19])[CH:16]=3)[N:7]=2)[CH2:3]1

参加物

4

反応物 2

HCID 71280491HCID 71280491、化合物HCID 178418573HCID 178418573、化合物

生成物 1

HCID 71280656HCID 71280656、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirring solution of N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(3-oxobutyl)imidazo[1,2-a]pyridine-3-carboxamide (F53) (40 mg, 0.083 mmol) in anhydrous THF (2 mL) at −78° C. under a stream of Argon was added methylmagnesium bromide (83 uL, 0.25 mmol). The reaction was stirred to room temperature for 30 minutes. The reaction was cooled to 0° C. and was quenched with saturated NH4Cl (2 mL). The crude product was extracted with ethylacetate. The organic was washed with water, brine and dried over anhydrous sodium sulfate. The solvent was concentrated and the crude product was purified by reverse phase preparative HPLC to give N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(3-hydroxy-3-methylbutyl)imidazo[1,2-a]pyridine-3-carboxamide (F54). 1H NMR (400 MHz, d6-DMSO) δ 10.18 (s, 1H), 9.36 (s, 1H), 8.68 (s, 1H), 8.08 (d, J=1.6 Hz, 1H), 7.86-7.82 (m, 2H), 7.65-7.62 (m, 1H), 7.51 (d, J=8.4 Hz, 1H), 3.91-3.84 (m, 1H), 3.25-3.04 (m, 4H), 2.78-2.73 (m, 2H), 2.37 (s, 3H), 1.71-1.67 (m, 2H), 1.16 (s, 6H). MS m/z 496.21 (M+1)+.

後処理

  1. temperatureThe reaction was cooled to 0° C.
  2. customwas quenched with saturated NH4Cl (2 mL)
  3. extractionThe crude product was extracted with ethylacetate
  4. washThe organic was washed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe solvent was concentrated
  7. customthe crude product was purified by reverse phase preparative HPLC

出典と根拠

ORDレコード
ord-6c86a82d19264e778771cdc3cb365016
出典データセット
uspto-grants-2015_12
特許番号
US09199981B2

反応ノート

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