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 983170노트

반응식

HRID 983170 반응식
[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

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21906603Chloroform isopropyl alcohol용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-a2edc60f9ff54e23974e2874294d4a64
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06861418B2

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