Hydrochloric Acid → {3,5-Dichloro-4-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]phenyl}methanol hydrochloride salt

HRID 626807ノート

反応式

HRID 626807 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:28])[C:9]=1[N:10]1[CH:27]=[C:13]2[C:14]([NH:19][C:20]3[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22][N:21]=3)=[N:15][CH:16]=[C:17]([F:18])[C:12]2=[N:11]1)[CH:5]=[O:6].[BH4-].[Na+].Cl>C(O)C.C1COCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([Cl:28])[C:9]=1[N:10]1[CH:27]=[C:13]2[C:14]([NH:19][C:20]3[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22][N:21]=3)=[N:15][CH:16]=[C:17]([F:18])[C:12]2=[N:11]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 866970833,5-Dichloro-4-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzaldehyde

生成物 1

HCID 69670988{3,5-Dichloro-4-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]phenyl}methanol hydrochloride salt収率 90.7%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3,5-dichloro-4-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzaldehyde (125 mg, 0.3 mmol) in ethanol (IMS grade, 5 mL) and THF (2 mL) was added sodium borohydride (14 mg, 0.36 mmol) and the reaction mixture was stirred at room temperature for 2 hours. The resultant mixture was partitioned between ethyl acetate and water and the layers were separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-1% methanol in ethyl acetate) to yield a solid, to which was added HCl (1.25 N in propan-2-ol, 10 mL) and the mixture was stirred at room temperature for 1 hour. The solid obtained was collected by filtration and dried to afford the title compound as an off-white solid (62 mg, 45% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.35 (br s, 1H), 8.97 (s, 1H), 8.36 (br s, 1H), 8.10 (d, J=3.5 Hz, 1H), 7.75 (s, 2H), 4.68 (s, 2H), 2.57 (s, 3H). LCMS (Method B): RT=2.89 min, m/z: 419 [M+H+].

後処理

  1. customThe resultant mixture was partitioned between ethyl acetate and water
  2. customthe layers were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel flash chromatography (0-1% methanol in ethyl acetate)
  8. customto yield a solid
  9. stirringthe mixture was stirred at room temperature for 1 hour
  10. customThe solid obtained
  11. filtrationwas collected by filtration
  12. customdried

出典と根拠

ORDレコード
ord-8910352a08764f3e8f5168487e8c430a
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

反応ノート

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