Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → 3-[1-[3,5-Dimethyl-4-(4-morpholin-4-yl-piperidine-1-carbonyl)-1H-pyrrol-2-yl]-meth-(Z)-ylidene]4-(3-fluoro-phenyl)-1,3-dihydro-indol-2-one

HRID 983170ノート

反応式

HRID 983170 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2/[C:10](=[CH:18]/[C:19]2[NH:23][C:22]([CH3:24])=[C:21]([C:25]([OH:27])=O)[C:20]=2[CH3:28])/[C:11](=[O:17])[NH:12]3)[CH:5]=[CH:6][CH:7]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH:56]1[CH2:61][CH2:60][CH:59]([N:62]2[CH2:67][CH2:66][O:65][CH2:64][CH2:63]2)[CH2:58][CH2:57]1.[Li+].[Cl-]>CN(C=O)C.C(Cl)(Cl)Cl.C(O)(C)C>[CH3:28][C:20]1[C:21]([C:25]([N:56]2[CH2:61][CH2:60][CH:59]([N:62]3[CH2:67][CH2:66][O:65][CH2:64][CH2:63]3)[CH2:58][CH2:57]2)=[O:27])=[C:22]([CH3:24])[NH:23][C:19]=1/[CH:18]=[C:10]1\[C:11](=[O:17])[NH:12][C:13]2[C:9]\1=[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[CH:16]=[CH:15][CH:14]=2

参加物

7

反応物 4

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 433294Lithium ChlorideHCID 7957244-MorpholinopiperidineHCID 697413865-[4-(3-Fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

生成物 1

HCID 600615833-[1-[3,5-Dimethyl-4-(4-morpholin-4-yl-piperidine-1-carbonyl)-1H-pyrrol-2-yl]-meth-(Z)-ylidene]4-(3-fluoro-phenyl)-1,3-dihydro-indol-2-one

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21906603Chloroform isopropyl alcohol溶媒

実験手順

5-[4-(3-Fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (1 eq.) and BOP (1.25 eq.) were suspended in DMF (5 mL) at rt and TEA (2.4 eq.) was added. After 15 mina, to the homogenous reaction mixture was added 4-piperidin-4-yl-morpholine (1.25 eq.) all at once. After stirring for 2 days, the reaction was added to a mixture of chloroform-isopropanol (5:1) and 5% aq. LiCl. The organic layer was separated, washed with 5% aq. LiCl (2×), 1M aq. NaOH (3×), brine, dried and concentrated. The residue was purified to give the titled compound

後処理

  1. customThe organic layer was separated
  2. washwashed with 5% aq. LiCl (2×), 1M aq. NaOH (3×), brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified

出典と根拠

ORDレコード
ord-a2edc60f9ff54e23974e2874294d4a64
出典データセット
uspto-grants-2005_03
特許番号
US06861418B2

反応ノート

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