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Methanol → N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-6-chlorobenzo[d]oxazol-2-amine

HRID 930292
ノート
印刷プレビュー

反応式

HRID 930292 の反応式
[Cl:1][C:2]1[CH:38]=[CH:37][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([F:36])=[C:14]([C@:16]4([CH3:35])[CH2:21][C@@H:20]([C:22]([F:25])([F:24])[F:23])[O:19][C:18]([NH:26]C(=O)C5C=CC=CC=5)=[N:17]4)[CH:15]=3)[O:8][C:4]=2[CH:3]=1.C1CCN2C(=NCCC2)CC1.CO>[NH4+].[Cl-].CCOC(C)=O>[NH2:26][C:18]1[O:19][C@H:20]([C:22]([F:25])([F:24])[F:23])[CH2:21][C@:16]([C:14]2[CH:15]=[C:10]([NH:9][C:7]3[O:8][C:4]4[CH:3]=[C:2]([Cl:1])[CH:38]=[CH:37][C:5]=4[N:6]=3)[CH:11]=[CH:12][C:13]=2[F:36])([CH3:35])[N:17]=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

6

反応物 3

HCID 887MethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86732122N-((4S,6S)-4-(5-((6-chlorobenzo[d]oxazol-2-yl)amino)-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide

生成物 1

HCID 86732124N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-6-chlorobenzo[d]oxazol-2-amine収率 8%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒
HCID 25517Ammonium Chloride溶媒

反応条件

温度
65 °C

実験手順

A mixture of N-((4S,6S)-4-(5-((6-chlorobenzo[d]oxazol-2-yl)amino)-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide (0.200 g, 0.366 mmol), DBU (0.072 mL, 0.475 mmol) and MeOH (3 mL) was stirred at 65° C. After 4 h, the mixture was diluted with saturated NH4Cl and EtOAc. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The crude was purified by silica gel chromatography: 0-100% in 15 min, then 100% EtOAc-hexane. The product was obtained as a white solid (67.4 mg, 91% pure). The crude was further purified by reverse phase HPLC: 10-100% in 16 min, MeCN in water with 0.1% TFA. The combined fractions were neutralized with solid Na2CO3, and extracted with DCM three times. The organic phase was dried over Na2SO4 and concentrated in vacuo. The product was obtained as a white solid (12.7 mg, 8% yield). MS m/z=443 [M+H]+. Calculated for C19H15ClF4N4O2: 442.8.

後処理

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude was purified by silica gel chromatography
  5. wait0-100% in 15 min
  6. customThe product was obtained as a white solid (67.4 mg, 91% pure)
  7. customThe crude was further purified by reverse phase HPLC
  8. wait10-100% in 16 min
  9. extractionextracted with DCM three times
  10. dry with materialThe organic phase was dried over Na2SO4
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-03c016153e1e4681ae132702694758d6
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09296734B2

反応ノート

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