Tetrahydrofuran → [5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophen-2-yl]-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

HRID 572287

反応式

HRID 572287 の反応式
[CH3:1][C:2]1[C:3]([C:11]2[S:15][C:14]([C:16]([OH:18])=O)=[CH:13][CH:12]=2)=[N:4][O:5][C:6]=1[C:7]([F:10])([F:9])[F:8].[NH:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH2:24][N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.C1COCC1.N1CCCCC1>C(N(CC)CC)C>[CH3:1][C:2]1[C:3]([C:11]2[S:15][C:14]([C:16]([N:19]3[CH2:23][CH2:22][CH2:21][C@H:20]3[CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:18])=[CH:13][CH:12]=2)=[N:4][O:5][C:6]=1[C:7]([F:8])([F:9])[F:10]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 8082PiperidineHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 252109975-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid

生成物 1

HCID 25211285[5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophen-2-yl]-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone収率 85%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

Prepared from 5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and (S)-(+)-1-(2-pyrrolidinylmethyl)-pyrrolidine by the method described in Example 2 Method B reversing the order of addition such that solid acid chloride was added to a THF solution of triethylamine and piperidine derivative. The reaction mixture was evaporated to a solid, triturated and filtered with the aid of water, then washed with a saturated aqueous NaHCO3 solution followed by water to afford product as a pale yellow solid (88 mg, 85%). 1H NMR (CDCl3) 1.76 (m, 4H), 1.96-2.10 (m, 4H), 2.37 (d, J=1.3, 3H), 2.56-2.64 (m, 6H), 3.80 (m, 2H), 4.48 (m, 1H), 7.50 (d, J=4.0, 1H), 7.57 (br, 1H). 19F NMR −63.2. LC/MS 4.66 min, [M+1]+ 414.

後処理

  1. customThe reaction mixture was evaporated to a solid
  2. customtriturated
  3. filtrationfiltered with the aid of water
  4. washwashed with a saturated aqueous NaHCO3 solution

出典と根拠

ORDレコード
ord-378257bce9694a93b88713b80f692973
出典データセット
uspto-grants-2015_05
特許番号
US09029397B2

関連ノート

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