Sodium Carbonate → (R)-4-methyl-2-(6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzo[d]thiazol-2-ylamino)pentan-1-ol

HRID 2370532

反応式

Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:25]=[CH:24][C:12]3[N:13]=[C:14]([NH:16][C@H:17]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:18][OH:19])[S:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:26][N:27]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[N:28]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:22][CH:21]([CH3:23])[CH2:20][C@@H:17]([NH:16][C:14]1[S:15][C:11]2[CH:10]=[C:9]([O:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([C:30]4[CH:29]=[N:28][N:27]([CH3:26])[CH:31]=4)[CH:7]=3)[CH:25]=[CH:24][C:12]=2[N:13]=1)[CH2:18][OH:19]

参加物

反応条件

温度: 90 °C

実験手順

To the reaction mixture of (R)-2-(6-(2-chloropyridin-4-yloxy)benzo[d]thiazol-2-ylamino)-4-methylpentan-1-ol (12 mg, 31 μmol) in 400 μL of DME, 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (21 mg, 100 μmol), Pd(dppf)2Cl2 (7 mg, 8 μmol and aq. 2M Na2CO3 (100 μL, 200 μmol) were added. The reaction mixture was stirred at 90° C. for 24 hours. The reaction mixture filtered, purified on prep HPLC and evaporated in vaccuo to give (R)-4-methyl-2-(6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzo[d]thiazol-2-ylamino)pentan-1-ol as powder (4.2 mg). ES/MS m/z 424.1 (MH+).

後処理

additionwere added
filtrationThe reaction mixture filtered
custompurified on prep HPLC
customevaporated in vaccuo

出典と根拠

ORDレコード: ord-ef52756617d74dcd82fcff04f88c36f6
出典データセット: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08710048B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 2

反応条件

実験手順

後処理

出典と根拠

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