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

HRID 1037547Notes

Reaction equation

HRID 1037547 reaction equation
[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]

Participants

4

Reactant 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

Product 1

HCID 569627726-[(2-aminoethyl)(methylsulfonyl)amino]-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamideYield 95.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-11d6e17c8cb54e8ba6e6405696bc378f
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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