Trifluoroacetic acid → N-methyl-1-(5-(thiophen-2-yl)tetrazolo[1,5-a]pyrazin-8-yl)azetidin-3-amine

HRID 1045740ノート

反応式

HRID 1045740 の反応式
[CH3:1][N:2]([CH:10]1[CH2:13][N:12]([C:14]2[C:15]3[N:16]([N:25]=[N:26][N:27]=3)[C:17]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[CH:18][N:19]=2)[CH2:11]1)C(=O)OC(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:1][NH:2][CH:10]1[CH2:11][N:12]([C:14]2[C:15]3[N:16]([N:25]=[N:26][N:27]=3)[C:17]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[CH:18][N:19]=2)[CH2:13]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 58447026tert-Butyl methyl(1-(5-(thiophen-2-yl)tetrazolo[1,5-a]pyrazin-8-yl)azetidin-3-yl)carbamate

生成物 1

HCID 53391272N-methyl-1-(5-(thiophen-2-yl)tetrazolo[1,5-a]pyrazin-8-yl)azetidin-3-amine収率 73%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A 2 L round bottom flask was charged with tert-butyl methyl(1-(5-(thiophen-2-yl)tetrazolo[1,5-a]pyrazin-8-yl)azetidin-3-yl)carbamate (50 g, 0.13 mol) and dichloromethane (500 mL). To the solution was added trifluoroacetic acid (100 mL). The resulting slurry was stirred at room temperature for 2.5 h. Work-up: the reaction mixture was concentrated in vacuo. The residue was suspended in water (500 L) and treated with solid Na2CO3 (pH 10-11, there was un-dissolved Na2CO3 remaining). The solid was collected by filtration, re-suspended in water (500 mL×2) with stirring to remove Na2CO3. It was further washed with EtOH (500 mL), and dried to afford 27 g (73%) of the product as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ: 8.19 (s, 1H), 7.96 (dd, J=4.0, 0.8 Hz, 1H), 7.76 (dd, J=4.8, 0.8 Hz, 1H), 7.27 (dd, J=4.8, 4.0 Hz, 1H), 4.60 (br, 2H), 4.18 (br, 2H), 3.73 (m, 1H), 2.43 (br, 1H), 2.29 (s, 3H). MS m/z: 288 (M+H+).

後処理

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiontreated with solid Na2CO3 (pH 10-11, there was un-dissolved Na2CO3 remaining)
  3. filtrationThe solid was collected by filtration
  4. stirringwith stirring
  5. customto remove Na2CO3
  6. washIt was further washed with EtOH (500 mL)
  7. customdried

出典と根拠

ORDレコード
ord-6fc36dc68d424e87a52278a8a4304a0e
出典データセット
uspto-grants-2013_10
特許番号
US08569300B2

反応ノート

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