Dimethylformamide → HCID 67496481、化合物

HRID 1628234ノート

反応式

HRID 1628234 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.CN(C(ON1N=N[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:35]([O:39][C:40]([C@@H](CC1C=CC=CC=1)C(O)=O)=[O:41])([CH3:38])([CH3:37])[CH3:36].CC[N:55](C(C)C)[CH:56]([CH3:58])[CH3:57].CN(C=[O:66])C>>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:57](=[O:66])[C@@H:56]([NH:55][C:40](=[O:41])[O:39][C:35]([CH3:36])([CH3:37])[CH3:38])[CH2:58][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 447548695-Bromo-2-methoxypyridin-3-amineHCID 67089511HCID 67089511、化合物

生成物 1

HCID 67496481HCID 67496481、化合物収率 70%

反応条件

温度
50 °C

実験手順

To a 100 ml flask was added 5-bromo-2-methoxypyridin-3-amine 15.1.A (15 g, 74 mmole, available from Asymchem), HBTU (42 g, 111 mmoles), (S)-2-(tert-butoxycarbonyl)-3-phenylpropanoic acid (24 g, 89 mmole) of, 150 ml of DMF and 26 mL of DIEA. The reaction was stirred at 50° C. for 24 hours, at which time the reaction was quenched with water (500 ml) and extracted with EtAc (1000 ml). The organic layer was extracted three more times with water (200 mL) and the solvent was removed by rotary evaporation. The crude product was recrystallized in MeOH/H2O (3/1) to give (S)-tert-butyl 1-(5-bromo-2-methoxypyridin-3-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 15.1.B as white crystals (23.4 g, 70% yield).

後処理

  1. customwas quenched with water (500 ml)
  2. extractionextracted with EtAc (1000 ml)
  3. extractionThe organic layer was extracted three more times with water (200 mL)
  4. customthe solvent was removed by rotary evaporation
  5. customThe crude product was recrystallized in MeOH/H2O (3/1)

出典と根拠

ORDレコード
ord-98c455ab33aa41dcb405b098800b249a
出典データセット
uspto-grants-2014_07
特許番号
US08785468B2

反応ノート

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