1-Hydroxybenzotriazole → (S)-5-chloro-N-(2'-methoxy-2-(2,2,2-trifluoroacetamido)-5H-spiro[oxazole-4,9'-xanthene]-7'-yl)picolinamide

HRID 1970311ノート

反応式

HRID 1970311 の反応式
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:16][CH3:17])=[CH:9][CH:10]=3)[C@:5]3([CH2:21][O:20][C:19]([NH:22][C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])=[N:18]3)[C:4]=2[CH:3]=1.[Cl:29][C:30]1[CH:31]=[CH:32][C:33]([C:36](O)=[O:37])=[N:34][CH:35]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.CN(C=O)C.O>[Cl:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]([NH:1][C:2]2[CH:3]=[C:4]3[C:13]([O:12][C:11]4[CH:10]=[CH:9][C:8]([O:16][CH3:17])=[CH:7][C:6]=4[C@@:5]43[CH2:21][O:20][C:19]([NH:22][C:23](=[O:28])[C:24]([F:26])([F:25])[F:27])=[N:18]4)=[CH:14][CH:15]=2)=[O:37])=[N:34][CH:35]=1

参加物

8

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27628725-Chloro-2-picolinic acidHCID 86640720(S)-N-(2'-amino-7'-methoxy-5H-spiro[oxazole-4,9'-xanthene]-2-yl)-2,2,2-trifluoroacetamide

生成物 1

HCID 86640719(S)-5-chloro-N-(2'-methoxy-2-(2,2,2-trifluoroacetamido)-5H-spiro[oxazole-4,9'-xanthene]-7'-yl)picolinamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A 25 mL RBF containing a solution of (S)—N-(2′-amino-7′-methoxy-5H-spiro[oxazole-4,9′-xanthene]-2-yl)-2,2,2-trifluoroacetamide (0.058 g, 0.147 mmol), 5-chloropyridine-2-carboxylic acid (0.030 g, 0.190 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.045 g, 0.235 mmol) in DCM (4 mL) and DMF (0.25 mL) was treated with 1-hydroxy-1H-benzotriazole (0.014 g, 0.104 mmol) and stirred for 1.5 hrs at RT. The reaction was diluted with DCM (50 mL) and water (15 mL). The DCM layer was separated, dried over anhydrous sodium sulfate, and concentrated to dryness to yield (S)-5-chloro-N-(2′-methoxy-2-(2,2,2-trifluoroacetamido)-5H-spiro[oxazole-4,9′-xanthene]-7′-yl)picolinamide as a brownish solid. MS (ESI pos. ion) m/z: 533 (M+1).

後処理

  1. customThe DCM layer was separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-6a2c00154a3c4b01b359c35b1703783b
出典データセット
uspto-grants-2013_04
特許番号
US08426447B2

反応ノート

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