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4-Methylmorpholine → Isopropyl 2-(3-(3-hexylquinoline-8-carboxamido)phenoxy)acetate

HRID 472792
ノート
印刷プレビュー

反応式

HRID 472792 の反応式
[CH2:1]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][C:11]=2[C:17]([OH:19])=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:20][C:21]1[CH:22]=[C:23]([CH:32]=[CH:33][CH:34]=1)[O:24][CH2:25][C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27].CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C=O)C>[CH2:1]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][C:11]=2[C:17]([NH:20][C:21]1[CH:22]=[C:23]([CH:32]=[CH:33][CH:34]=1)[O:24][CH2:25][C:26]([O:28][CH:29]([CH3:30])[CH3:31])=[O:27])=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10608474Isopropyl 2-(3-aminophenoxy)acetateHCID 666608943-Hexylquinoline-8-carboxylic acid

生成物 1

HCID 66660805Isopropyl 2-(3-(3-hexylquinoline-8-carboxamido)phenoxy)acetate収率 87.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-hexylquinoline-8-carboxylic acid (170 mg, 0.66 mmol), isopropyl 2-(3-aminophenoxy)acetate (207 mg, 0.99 mmol) and N-methylmorpholine (0.18 mL, 1.65 mmol) in DMF (2.0 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (380 mg, 1.0 mmol) and the solution was stirred at room temperature for 16 h. The DMF was removed in vacuo and the residue was partitioned between EtOAc and water. The organic phase was washed with saturated aqueous NaHCO3 (2×) then dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified on 12 g silica gel eluting (17:3 hexanes/EtOAc) to afford 259 mg (87%) of isopropyl 2-(3-(3-hexylquinoline-8-carboxamido)phenoxy)acetate.

後処理

  1. customThe DMF was removed in vacuo
  2. customthe residue was partitioned between EtOAc and water
  3. washThe organic phase was washed with saturated aqueous NaHCO3 (2×)
  4. dry with materialthen dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified on 12 g silica gel eluting (17:3 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-ba8da0b802cf4abab4f1e60353c7eef4
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08633220B2

反応ノート

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