Methanol → 6-amino-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide

HRID 1037526노트

반응식

HRID 1037526 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]([O-])=O)[C:13]([CH:21]4[CH2:23][CH2:22]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[Cl-].[NH4+].CO>C(O)C.O.C(Cl)Cl.[Fe]>[NH2:24][C:12]1[C:13]([CH:21]2[CH2:23][CH2:22]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

8

반응물 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 677763242-(4-bromophenyl)-5-cyclopropyl-N-methyl-6-nitro-2H-indazole-3-carboxamide

생성물 1

HCID 675127246-amino-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide수율 69.2%

시약·촉매·용매 4

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매2회HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

To a suspension of compound (viii) (500 mg, 1.20 mmol) in a mixture of ethanol (30 mL) and water (6 mL) was added ammonium chloride (450 mg, 8.43 mmol) followed by iron powder (470 mg, 8.43 mmol). The mixture was heated to 80° C. and stirred vigorously for 90 min. After cooling to RT, 5% MeOH in DCM solution (50 mL) was added to the reaction mixture. The resulting suspension was filtered through celite and washed with MeOH. The filtrate was concentrated in vacuo to give a yellow solid which was then suspended in water (40 mL) and filtered. The solid was collected and dried to give 6-amino-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide (ix) (320 mg, 68%) as a yellow solid. ESI-MS m/z calculated for [M+H]+: 385.07/387.06; found: 385.12/387.10.

후처리

  1. temperatureAfter cooling to RT
  2. filtrationThe resulting suspension was filtered through celite
  3. washwashed with MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a yellow solid which
  6. filtrationfiltered
  7. customThe solid was collected
  8. customdried

출처 및 근거

ORD 기록
ord-ea654436141d4bbb9aa3ffd62288db25
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546389B2

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