Water → tert-butyl (2-(((6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methyl)amino)ethyl)(methyl)carbamate

HRID 475313ノート

反応式

HRID 475313 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=O)[C:5]2[CH:6]=[N:7][N:8]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:9]=2[CH:10]=1.[NH2:19][CH2:20][CH2:21][N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].[BH4-].[Na+].O>CO>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([CH2:17][NH:19][CH2:20][CH2:21][N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 2756424N-Boc-N-methylethylenediamineHCID 4311764Sodium borohydrideHCID 866947626-Fluoro-1-tetrahydropyran-2-yl-indazole-4-carbaldehyde

生成物 1

HCID 86694764tert-butyl (2-(((6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methyl)amino)ethyl)(methyl)carbamate収率 103.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 6-fluoro-1-tetrahydropyran-2-yl-indazole-4-carbaldehyde (175 mg, 0.71 mmol) in MeOH (7 mL) was added tert-butyl N-(2-aminoethyl)-N-methyl-carbamate (184 mg, 1.06 mmol). The reaction was stirred at RT for 4 h, and then NaBH4 (35.4 mg, 0.92 mmol) was added. The reaction mixture was stirred at RT for 4 h and water was added. MeOH was removed under reduced pressure and the residue was diluted with 1N NaOH solution. The aqueous solution extracted with twice with EtOAc. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to obtain crude tert-butyl (2-(((6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methyl)amino)ethyl)(methyl)carbamate (300 mg, quantitative yield). MS (ESI) m/z: 407.2 [M+1]+.

後処理

  1. stirringThe reaction mixture was stirred at RT for 4 h
  2. customMeOH was removed under reduced pressure
  3. additionthe residue was diluted with 1N NaOH solution
  4. extractionThe aqueous solution extracted with twice with EtOAc
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f297cee408e9425293141b0c698be63f
出典データセット
uspto-grants-2014_01
特許番号
US08637537B2

反応ノート

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