Triethylamine → Tert-butyl n-heptyl-n-[2-[4-[2-(7-trifluoromethylbenzoxazol-2-ylthio)ethyl]piperazin-1-yl]ethyl]carbamate

HRID 1064847ノート

反応式

HRID 1064847 の反応式
[CH2:1]([N:8]([CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH2:25]O)[CH2:20][CH2:19]1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(N(CC)CC)C.CS(Cl)(=O)=O.[SH:39][C:40]1[O:41][C:42]2[C:48]([C:49]([F:52])([F:51])[F:50])=[CH:47][CH:46]=[CH:45][C:43]=2[N:44]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.CN(C)C1C=CN=CC=1.CN(C=O)C>[CH2:1]([N:8]([CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][S:39][C:40]2[O:41][C:42]3[C:48]([C:49]([F:52])([F:51])[F:50])=[CH:47][CH:46]=[CH:45][C:43]=3[N:44]=2)[CH2:20][CH2:19]1)[C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:14])[CH3:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

参加物

9

反応物 5

HCID 8471Triethylamine2 回HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chloride2 回HCID 22272782tert-butyl N-heptyl-N-[2-[4-(2-hydroxyethyl)piperazin-1-yl]ethyl]carbamateHCID 178506117HCID 178506117、化合物

生成物 1

HCID 22272608Tert-butyl n-heptyl-n-[2-[4-[2-(7-trifluoromethylbenzoxazol-2-ylthio)ethyl]piperazin-1-yl]ethyl]carbamate収率 37%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of this alcohol (500 mg, 1.35 mmol) in THF (10 ml) were added triethylamine (180 mg, 1.78 mmol) and 4-(dimethylamino) pyridine (16 mg, 0.13 mmol), and then methanesulfonyl chloride (190 mg, 1.66 mmol) was dropped there into with ice-cooling and stirred for 20 minutes. Further, to the same solution were added triethylamine (45 mg, 0.44 mmol) and methanesulfonyl chloride (45 mg, 0.39 mmol) was dropped thereinto with ice-cooling and stirred for 1 hour. The reaction solution was filtered and the filtrate was concentrated in vacuo. The resulting residue was dissolved in DMF (3 ml), and the resulting solution was dropped into a solution of 2-mercapto-7-trifluoromethylbenzoxazole (310 mg, 1.41 mmol) and potassium carbonate (280 mg, 2.03 mmol) in DMF (7 ml) and stirred at 80° C. for 90 minutes. The reaction solution was concentrated in vacuo and the resulting residue was filtered off with ether. The filtrate was concentrated in vacuo and the resulting residue was purified by a silica gel column chromatography (silica gel 35 g, developing solvent; hexane:acetone=10:1) to provide 283 mg (yield 37%) of tert-butyl N-heptyl-N-[2-[4-[2-(7-trifluoromethylbenzoxazol-2-ylthio)ethyl]piperazin-1-yl]ethyl]carbamate as pale yellow oil.

後処理

  1. temperaturecooling
  2. additionwas dropped
  3. temperaturewith ice-cooling
  4. stirringstirred for 1 hour
  5. filtrationThe reaction solution was filtered
  6. concentrationthe filtrate was concentrated in vacuo
  7. dissolutionThe resulting residue was dissolved in DMF (3 ml)
  8. stirringstirred at 80° C. for 90 minutes
  9. concentrationThe reaction solution was concentrated in vacuo
  10. filtrationthe resulting residue was filtered off with ether
  11. concentrationThe filtrate was concentrated in vacuo
  12. customthe resulting residue was purified by a silica gel column chromatography (silica gel 35 g, developing solvent; hexane:acetone=10:1)

出典と根拠

ORDレコード
ord-aa8bcf8c8a7e49a0a44930246cfca2f9
出典データセット
uspto-grants-2005_11
特許番号
US06969711B2

反応ノート

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