Diisopropylethylamine → HCID 51051182、化合物

HRID 1694383

反応式

HRID 1694383 の反応式
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17](OC)=[O:18])[CH:10]=[CH:9]2)=[CH:5][CH:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:49][C:50]1([C:53]2[CH:62]=[CH:61][C:56]([C:57]([O:59][CH3:60])=[O:58])=[CH:55][CH:54]=2)[CH2:52][CH2:51]1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CCOC(C)=O.CN(C=O)C>[F:23][C:2]([F:1])([F:24])[C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]([NH:49][C:50]3([C:53]4[CH:62]=[CH:61][C:56]([C:57]([O:59][CH3:60])=[O:58])=[CH:55][CH:54]=4)[CH2:52][CH2:51]3)=[O:18])[CH:10]=[CH:9]2)=[CH:5][CH:4]=1

参加物

8

反応物 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45140209Methyl 4-(1-aminocyclopropyl)benzoateHCID 57434482HCID 57434482、化合物

生成物 1

HCID 51051182HCID 51051182、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Methyl 1-[4-(trifluoromethyl)benzyl]-1H-indole-7-carboxylate (30.8 g, 97 mmol), HATU (38.6 g, 101 mmol) and methyl 4-(1-aminocyclopropyl)benzoate (24.9 g, 130 mmol) were added to DMF (483 ml). The solution was cooled in an ice bath and DIPEA (50.6 ml, 290 mmol) was added. The mixture was aged overnight at RT and 500 ml of EtOAc was added. The mixture was then poured into 2 L of NaHCO3 (½ sat.). The layers were cut and the aqueous layer was washed 2 more times with DCM. The combined organic layers were washed with brine and dried with Na2SO4. The solvent was removed and the crude mixture purified by flash chromatography on silica gel. 1H NMR (500 MHz, DMSO-d6): δ 9.18 (s, 1H), 7.75 (m, 3H), 7.60 (d, 2H), 7.45 (d, 1H), 7.40 (d, 1H), 7.20 (d, 2H), 7.15 (t, 1H), 6.90 (d, 2H), 6.65 (d, 1H), 5.70 (s, 2H), 3.85 (s, 3H), 1.20 (m, 2H), 0.95 (m, 2H).

後処理

  1. temperatureThe solution was cooled in an ice bath
  2. washthe aqueous layer was washed 2 more times with DCM
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed
  6. customthe crude mixture purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-7b965da848074bbd87637f60839e13b8
出典データセット
uspto-grants-2012_04
特許番号
US08158671B2

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