Hydrazine hydrate (1:1) → 6-[(2-aminoethyl)(methylsulfonyl)amino]-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide

HRID 1037547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1037547
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]([NH:19][CH3:20])=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([N:24]([CH2:29][CH2:30][N:31]4C(=O)C5C(=CC=CC=5)C4=O)[S:25]([CH3:28])(=[O:27])=[O:26])[C:13]([CH:21]4[CH2:23][CH2:22]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.O.NN>C(O)C>[NH2:31][CH2:30][CH2:29][N:24]([S:25]([CH3:28])(=[O:26])=[O:27])[C:12]1[C:13]([CH:21]2[CH2:22][CH2:23]2)=[CH:14][C:15]2[C:10]([CH:11]=1)=[N:9][N:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[C:16]=2[C:17]([NH:19][CH3:20])=[O:18]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 569627712-(4-bromophenyl)-5-cyclopropyl-6-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl](methylsulfonyl)amino}-N-methyl-2H-indazole-3-carboxamide

Produkt 1

HCID 569627726-[(2-aminoethyl)(methylsulfonyl)amino]-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamideAusbeute 95,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of Compound (6) (92 mg, 0.14 mmol) and hydrazine hydrate (0.15 mL) in ethanol (7 mL) was stirred at RT for 16 h. The resulting suspension was filtered and the filtrate was concentrated to give a crude oil which then was partitioned between EtOAc (5 mL) and water (2 mL). The organic phase was separated and the aqueous phase was extracted with EtOAc (3×3 mL). The combined organic phase was dried (MgSO4) and the solvent was removed in vacuo to give 6-[(2-aminoethyl)(methylsulfonyl)amino]-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide (7) (68 mg, 93%). ESI-MS m/z calculated for [M+H]+: 506.08/508.09; found: 505.88/507.89.

Aufarbeitung

  1. filtrationThe resulting suspension was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give a crude oil which
  4. customthen was partitioned between EtOAc (5 mL) and water (2 mL)
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with EtOAc (3×3 mL)
  7. dry with materialThe combined organic phase was dried (MgSO4)
  8. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-11d6e17c8cb54e8ba6e6405696bc378f
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546389B2

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