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

HRID 1970311노트

반응식

HRID 1970311 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-6a2c00154a3c4b01b359c35b1703783b
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426447B2

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