ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Dimethylformamide → N-{5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-chloro-3-pyridinyl}methanesulfonamide

HRID 1695722
ノート
印刷プレビュー

反応式

HRID 1695722 の反応式
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[C:16]([Sn](C)(C)C)[CH:15]=[C:14]([NH2:23])[C:13]=3[CH:12]=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C.Br[C:30]1[CH:31]=[C:32]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[C:33]([Cl:36])=[N:34][CH:35]=1>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:23][C:14]1[CH:15]=[C:16]([C:30]2[CH:31]=[C:32]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[C:33]([Cl:36])=[N:34][CH:35]=2)[CH:17]=[C:18]2[C:13]=1[CH:12]=[N:11][N:10]2[S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 582557431-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amineHCID 59519513N-(5-bromo-2-chloro-3-pyridinyl)methanesulfonamide

生成物 1

HCID 58255829N-{5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-chloro-3-pyridinyl}methanesulfonamide収率 19.8%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 6344Dichloromethane溶媒

反応条件

温度
120 °C

実験手順

Four identical reactions were carried out in a 20 ml microwave vial, each using one quarter of the quantities stated. They were then combined for work-up and purification. A solution of a quarter of 1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (4.329 g, 9.93 mmol) in a quarter of DMF (24 ml) was treated with a quarter of N-(5-bromo-2-chloro-3-pyridinyl)methanesulfonamide (3.26 g, 11.42 mmol) followed by a quarter of Pd(PPh3)4 (1.032 g, 0.893 mmol). Each vial was heated at 120° C. for 50 mins in a Biotage Initiator. The orange solutions were combined and loaded onto a 20 g silica cartridge, and the vials washed with methanol (10 ml) which was also loaded onto the cartridge which was then eluted with methanol. Then eluants were evaporated to leave an orange oil. This was diluted with DCM (10 ml) and loaded directly and evenly onto 2×100 g silica cartridges. These were eluted with 0-100% ethyl acetate/cyclohexane over 80 mins using the Flashmaster II. Appropriate pure fractions were combined and evaporated to give the title compound as a yellow solid (0.939 g).

後処理

  1. customThey were then combined for work-up and purification
  2. washthe vials washed with methanol (10 ml) which
  3. washwas then eluted with methanol
  4. customThen eluants were evaporated
  5. customto leave an orange oil
  6. washThese were eluted with 0-100% ethyl acetate/cyclohexane over 80 mins
  7. customevaporated

出典と根拠

ORDレコード
ord-0c2976a389ba4c82a35beae9b02dad10
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08163743B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート