Diisopropylethylamine → (5R)-5-ethyl-5-methyl-3-[6-(7-methylspiro[2H-benzofuran-3,1'-cyclopropane]-4-yl)oxy-3-pyridyl]imidazolidine-2,4-dione

HRID 527715ノート

反応式

HRID 527715 の反応式
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.CCN(C(C)C)C(C)C.[CH3:22][C:23]1[C:28]2[O:29][CH2:30][C:31]3([CH2:33][CH2:32]3)[C:27]=2[C:26]([O:34][C:35]2[N:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=2)=[CH:25][CH:24]=1.Cl.[NH2:43][C@:44]([CH3:51])([CH2:49][CH3:50])[C:45](OC)=[O:46]>C(Cl)Cl>[CH2:49]([C@@:44]1([CH3:51])[NH:43][C:2](=[O:4])[N:41]([C:38]2[CH:39]=[N:40][C:35]([O:34][C:26]3[C:27]4[C:31]5([CH2:30][O:29][C:28]=4[C:23]([CH3:22])=[CH:24][CH:25]=3)[CH2:33][CH2:32]5)=[CH:36][CH:37]=2)[C:45]1=[O:46])[CH3:50]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 13018906(R)-2-Amino-2-methyl-butyric acid methyl ester hydrochlorideHCID 679599396-(7-methylspiro[2H-benzofuran-3,1'-cyclopropane]-4-yl)oxypyridin-3-amine2 回

生成物 1

HCID 57411182(5R)-5-ethyl-5-methyl-3-[6-(7-methylspiro[2H-benzofuran-3,1'-cyclopropane]-4-yl)oxy-3-pyridyl]imidazolidine-2,4-dione

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

To a solution of triphosgene (30 mg, 0.1 mmol) in dry DCM (1 ml) at 0° C., under nitrogen atmosphere, DIPEA (0.175 ml, 1.0 mmol) was added followed by the addition (slowly added) of a solution of 6-(7-methylspiro[2H-benzofuran-3,1′-cyclopropane]-4-yl)oxypyridin-3-amine (Intermediate 158, 27 mg, 0.1 mmol) in dry DCM (2 ml) and the reaction mixture was stirred for 15 minutes at the same temperature. After that a solution of Methyl (R)-2-amino-2-methyl-butyrate hydrochloride (33 mg, 0.2 mmol) in dry DCM (2 ml) was added and the reaction mixture was stirred for 30 minutes at 0° C. The reaction was quenched with a 1M aqueous solution of HCl (5 ml), diluted with DCM (10 ml) and two phases were separated. The organic layer was washed with brine (10 ml), dried (Na2SO4), filtered and evaporated affording the urea intermediate as yellow foam.

後処理

  1. additionfollowed by the addition (
  2. stirringthe reaction mixture was stirred for 30 minutes at 0° C
  3. customThe reaction was quenched with a 1M aqueous solution of HCl (5 ml)
  4. additiondiluted with DCM (10 ml) and two phases
  5. customwere separated
  6. washThe organic layer was washed with brine (10 ml)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

出典と根拠

ORDレコード
ord-711e4ca33d2f434db9f8507cf415fa8f
出典データセット
uspto-grants-2016_05
特許番号
US09346790B2

反応ノート

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