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Hydrochloric Acid → (6R,13R)-9-fluoro-13-methyl-2,11,15,19,20,23-hexazapentacyclo[15.5.2.17,11.02,6.020,24]pentacosa-1(23),7,9,17(24),18,21-hexaene-16,25-dione

HRID 1426974
ノート
印刷プレビュー

反応式

HRID 1426974 の反応式
[NH2:1][CH2:2][C@@H:3]([CH3:31])[CH2:4][N:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]2[CH:22]=[CH:21][N:20]3[N:23]=[CH:24][C:25]([C:26](OC)=[O:27])=[C:19]3[N:18]=2)[C:6]1=[O:30].[OH-].[Li+].Cl.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>C1COCC1.CO.CN(C=O)C>[F:11][C:9]1[CH:8]=[C:7]2[C:6](=[O:30])[N:5]([CH:10]=1)[CH2:4][C@H:3]([CH3:31])[CH2:2][NH:1][C:26](=[O:27])[C:25]1=[C:19]3[N:18]=[C:17]([CH:22]=[CH:21][N:20]3[N:23]=[CH:24]1)[N:13]1[C@@H:12]2[CH2:16][CH2:15][CH2:14]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67471049methyl 5-((R)-2-(1-((R)-3-amino-2-methylpropyl)-5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

生成物 1

HCID 54670442(6R,13R)-9-fluoro-13-methyl-2,11,15,19,20,23-hexazapentacyclo[15.5.2.17,11.02,6.020,24]pentacosa-1(23),7,9,17(24),18,21-hexaene-16,25-dione収率 10.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21899815MeOH tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a solution of methyl 5-((R)-2-(1-((R)-3-amino-2-methylpropyl)-5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (65 mg, 0.15 mmol) in THF/MeOH (6 mL/2 mL) was added lithium hydroxide (455 μL, 0.91 mmol). The reaction was stirred at 70° C. for 3 hours, then quenched with hydrogen chloride (910 μL, 0.91 mmol). The solvent was removed under reduced pressure and the residue was dried under high vacuum. To the resulting crude residue was added DMF (10 mL), HATU (115 mg, 0.30 mmol) and N-ethyl-N-isopropylpropan-2-amine (78 mg, 0.61 mmol). The reaction was stirred for 3 hours, and the solvent was removed under reduced pressure. The residue was purified by silica column chromatography, eluting with 10% MeOH/EtOAc to afford the title compound (6.0 mg, 10% yield). MS (apci) m/z=397.3 (M+H).

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was dried under high vacuum
  3. stirringThe reaction was stirred for 3 hours
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica column chromatography
  6. washeluting with 10% MeOH/EtOAc

出典と根拠

ORDレコード
ord-97121a83eec34d97af5f84c9b407753c
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08933084B2

反応ノート

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