4-[4-[[4-Amino-5-(3-fluorobenzoyl)-2-thiazolyl]amino]phenyl]-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester → [4-Amino-2-[[4-(1-piperazinyl)phenyl]amino]-5-thiazolyl](3-fluorophenyl)methanone

HRID 2213907

反応式

HRID 2213907 の反応式
[NH2:1][C:2]1[N:3]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)=[CH:19][CH:18]=2)[S:5][C:6]=1[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=1.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[NH2:1][C:2]1[N:3]=[C:4]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:21][CH:22]=2)[S:5][C:6]=1[C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=1)=[O:15]

参加物

3

反応物 2

HCID 101176544-[4-[[4-Amino-5-(3-fluorobenzoyl)-2-thiazolyl]amino]phenyl]-1-piperazinecarboxylic acid, 1,1-dimethylethyl esterHCID 21863450Trifluoroacetic acid methylene chloride

生成物 1

HCID 9800951[4-Amino-2-[[4-(1-piperazinyl)phenyl]amino]-5-thiazolyl](3-fluorophenyl)methanone収率 100.6%

実験手順

A mixture of 4-[4-[[4-amino-5-(3-fluorobenzoyl)-2-thiazolyl]amino]phenyl]-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (75 mg, 0.15 mmol) (from Step A above) and a solution of TFA/CH2Cl2 (1:1; 1.5 mL) was gently shaken for 1.5 h. The solution was evaporated in vacuo. To the residue was added resin-bound N,N-diisopropylethylamine (2.5 g, loading capacity: 3.8 mmol/g from Argonaut, Inc.) and CH2Cl2 (15 mL). After shaking overnight, the mixture was filtered and washed successively with CH3OH and CH2Cl2. The solvent was evaporated in vacuo and the residue was triturated by diethyl ether/hexanes (1/9) to afford [4-amino-2-[[4-(1-piperazinyl)phenyl]amino]-5-thiazolyl](3-fluorophenyl)methanone (60 mg, 100%).

後処理

  1. customThe solution was evaporated in vacuo
  2. additionTo the residue was added resin-bound N,N-diisopropylethylamine (2.5 g, loading capacity: 3.8 mmol/g from Argonaut, Inc.) and CH2Cl2 (15 mL)
  3. filtrationthe mixture was filtered
  4. washwashed successively with CH3OH and CH2Cl2
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was triturated by diethyl ether/hexanes (1/9)

出典と根拠

ORDレコード
ord-fcabc2c1d9cf465b9bdd00c79386e7f2
出典データセット
uspto-grants-2006_09
特許番号
US07105670B2

関連ノート

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