4-Methylmorpholine → HCID 178481055、化合物

HRID 467675

反応式

HRID 467675 の反応式
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]([NH:12][C:13]3[C:14]([C:19](O)=[O:20])=[N:15][N:16]([CH3:18])[CH:17]=3)=[O:11])[C:7]([NH:22][C:23]3[CH:24]=[N:25][CH:26]=[N:27][CH:28]=3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:60][C:61]1([CH3:66])[CH2:65][CH2:64][CH2:63][NH:62]1>CN(C=O)C>[CH:1]1([C:4]2[N:9]=[C:8]([C:10](=[N:12][C:13]3[C:14]([C:19]([N:62]4[CH2:63][CH2:64][CH2:65][C:61]4([CH3:66])[CH3:60])=[O:20])=[N:15][N:16]([CH3:18])[CH:17]=3)[OH:11])[C:7]([NH:22][C:23]3[CH:28]=[N:27][CH:26]=[N:25][CH:24]=3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 4147732,2-DimethylpyrrolidineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 701164844-{[6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carbonyl]-amino}-1-methyl-1H-pyrazole-3-carboxylic acid

生成物 1

HCID 178481055HCID 178481055、化合物収率 7.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To stirred solution of 4-{[6-cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carbonyl]-amino}-1-methyl-1H-pyrazole-3-carboxylic acid (70 mg, 0.18 mmol) in DMF were sequentially added N-methylmorpholine (0.12 ml, 0.9 mmol), HBTU (210 mg, 0.55 mmol), and 2,2-dimethylpyrrolidine (35 mg, 0.36 mmol) at rt, and the reaction mixture was allowed to stirr overnight. The solvent was removed in vacuo, and the residue was dissolved in EtOAc (10 ml), and was washed with aqueous NaHCO3 solution and water. The aqueous layer was back-extracted with EtOAc, and the combined organic layer was dried (Na2SO4), filtered, and evaporated in vacuo. The crude product was purified by prep. HPLC (column: Gemini C18 (250×21.2 mm, 5μ); elution with a gradient of 0.05% aqueous TFA solution/acetonitrile) to give the title compound (6 mg, 6%) as sticky yellow solid.

後処理

  1. customat rt
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in EtOAc (10 ml)
  4. washwas washed with aqueous NaHCO3 solution and water
  5. extractionThe aqueous layer was back-extracted with EtOAc
  6. dry with materialthe combined organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe crude product was purified by prep
  10. washelution with a gradient of 0.05% aqueous TFA solution/acetonitrile)

出典と根拠

ORDレコード
ord-3c976982d1f94f6f97fdadaafff57e62
出典データセット
uspto-grants-2014_01
特許番号
US08623866B2

関連ノート

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