1,2-Dimethoxyethane → 5-[(4-fluoro-1-methylpiperidin-4-yl)carbonyl]-N-(5-fluoro-2-vinylpyrimidin-4-yl)-6,6-dimethyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-amine

HRID 331073

反応式

HRID 331073 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:10]3[CH2:16][N:15]([C:17]([C:19]4([F:26])[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]4)=[O:18])[C:14]([CH3:28])([CH3:27])[C:11]=3[NH:12][N:13]=2)[C:5]([F:29])=[CH:4][N:3]=1.[CH3:30][C:31]1(C)C(C)(C)OB(C=C)O1.C([O-])([O-])=O.[Na+].[Na+].COCCOC>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].O>[F:26][C:19]1([C:17]([N:15]2[CH2:16][C:10]3[C:9]([NH:8][C:6]4[C:5]([F:29])=[CH:4][N:3]=[C:2]([CH:30]=[CH2:31])[N:7]=4)=[N:13][NH:12][C:11]=3[C:14]2([CH3:28])[CH3:27])=[O:18])[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 59333922[3-(2-Chloro-5-fluoro-pyrimidin-4-ylamino)-6,6-dimethyl-4,6-dihydro-1H-pyrrolo[3,4-c]pyrazol-5-yl]-(4-fluoro-1-methyl-piperidin-4-yl)-methanone

生成物 1

HCID 593340165-[(4-fluoro-1-methylpiperidin-4-yl)carbonyl]-N-(5-fluoro-2-vinylpyrimidin-4-yl)-6,6-dimethyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-amine

試薬・触媒・溶媒 2

HCID 53485975CID 53485975触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

To a pressure vessel was added starting material [3-(2-Chloro-5-fluoro-pyrimidin-4-ylamino)-6,6-dimethyl-4,6-dihydro-1H-pyrrolo[3,4-c]pyrazol-5-yl]-(4-fluoro-1-methyl-piperidin-4-yl)-methanone (0.375 g, 0.881 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2 dioxaborolane (0.407 g, 2.64 mmol), Na2CO3 (0.280 g, 2.64 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.144 g, 0.176 mmol) followed by DME (10 mL) and water (2 mL). The reaction mixture was purged with argon for 2 min, then heat to 100° C. for 15 h. The volatiles were concentrated in vacuo and the residue redissolved in EtOAc (15 mL). The organic layer was washed with water (10 mL), dried over MgSO4, filtered, and concentrated to give the desired product G1(i) as a brown foam (0.35 g, 95%). Mass Spectrum: Calcd for C20H26N7OF2 (M+H): 418. Found: 418.

後処理

  1. additionTo a pressure vessel was added
  2. customThe reaction mixture was purged with argon for 2 min
  3. concentrationThe volatiles were concentrated in vacuo
  4. dissolutionthe residue redissolved in EtOAc (15 mL)
  5. washThe organic layer was washed with water (10 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-8d93b933d4c24472b792407d57d3540a
出典データセット
uspto-grants-2014_11
特許番号
US08877761B2

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