Diisopropylethylamine → HCID 178467766、化合物

HRID 2202279ノート

反応式

HRID 2202279 の反応式
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH2:26]([O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[C@H:35]([C:39]([NH:41][C:42]1[CH:47]=[C:46]([F:48])[C:45]([C:49]([CH3:55])([CH3:54])[CH2:50][O:51][CH2:52][CH3:53])=[C:44]([F:56])[CH:43]=1)=[O:40])[NH:34][CH2:33][CH2:32]2)[CH3:27].[C:57]([O:61][C:62](=[O:71])[CH2:63][C@@H:64]1[CH2:67][C@H:66]([C:68](O)=[O:69])[CH2:65]1)([CH3:60])([CH3:59])[CH3:58].CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH2:26]([O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[C@H:35]([C:39](=[O:40])[NH:41][C:42]1[CH:47]=[C:46]([F:48])[C:45]([C:49]([CH3:54])([CH3:55])[CH2:50][O:51][CH2:52][CH3:53])=[C:44]([F:56])[CH:43]=1)[N:34]([C:68]([C@@H:66]1[CH2:65][C@H:64]([CH2:63][C:62]([O:61][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:71])[CH2:67]1)=[O:69])[CH2:33][CH2:32]2)[CH3:27]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118622710(R)-6-ethoxy-N-(4-(1-ethoxy-2-methylpropan-2-yl)-3,5-difluorophenyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxamide hydrochlorideHCID 178451083HCID 178451083、化合物

生成物 1

HCID 178467766HCID 178467766、化合物収率 97.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

HATU (90 mg, 0.24 mmol) was added to a solution of (R)-6-ethoxy-N-(4-(1-ethoxy-2-methylpropan-2-yl)-3,5-difluorophenyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxamide hydrochloride (101 mg, 0.22 mmol), cis-3-(2-(tert-butoxy)-2-oxoethyl)cyclobutanecarboxylic acid (50.8 mg, 0.24 mmol) and DIEA (0.085 mL, 0.47 mmol) in DMF (2 mL) at room temperature, and the mixture was stirred overnight at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 3→50% ethyl acetate/hexane) to give tert-butyl 2-(cis-3-((R)-6-ethoxy-1-((4-(1-ethoxy-2-methylpropan-2-yl)-3,5-difluorophenyl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)cyclobutyl)acetate (135 mg, 0.215 mmol, quant.).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 3→50% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-743209d95deb4b9b9e178c66fb643661
出典データセット
uspto-grants-2016_06
特許番号
US09365520B2

反応ノート

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