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

HRID 1037547노트

반응식

HRID 1037547 반응식
[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]

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-11d6e17c8cb54e8ba6e6405696bc378f
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546389B2

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