4-Hydroxy-3-nitrobenzoic acid → (S)-N-((3-Fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)-4-hydroxy-3-nitrobenzamide

HRID 509415

반응식

HRID 509415 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[F:48][C:49]1[C:50]([C@H:55]([C:57]2[CH:62]=[CH:61][C:60]([C:63]([F:66])([F:65])[F:64])=[CH:59][CH:58]=2)[NH2:56])=[N:51][CH:52]=[CH:53][CH:54]=1.Cl.FC(F)(F)C1C=CC([C@@H](C2C(C(F)(F)F)=CC=CN=2)N)=CC=1>O.CN(C=O)C>[F:48][C:49]1[C:50]([C@H:55]([C:57]2[CH:62]=[CH:61][C:60]([C:63]([F:65])([F:66])[F:64])=[CH:59][CH:58]=2)[NH:56][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([OH:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)=[N:51][CH:52]=[CH:53][CH:54]=1

참가 물질

8

반응물 5

HCID 120334-Hydroxy-3-nitrobenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71144279(S)-(3-Fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methanamine HydrochlorideHCID 86687962(S)-(4-(Trifluoromethyl)phenyl)(3-(trifluoromethyl)pyridin-2-yl)methanamine Hydrochloride

생성물 1

HCID 71144294(S)-N-((3-Fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)-4-hydroxy-3-nitrobenzamide

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-hydroxy-3-nitrobenzoic acid (285 mg, 1.556 mmol) and DMF (5 mL), were added DIPEA (0.69 mL, 3.96 mmol) and HATU (612 mg, 1.611 mmol). After stirring for 45 min, (S)-(3-fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methanamine hydrochloride (380 mg, 1.239 mmol, Intermediate 2) was added in one portion. The reaction was stirred at room temperature for 5 h and was then diluted with water (50 mL). The aqueous solution was extracted with EtOAc (3×20 mL). The combined EtOAc layers were concentrated in vacuo and adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (12 g), eluting with 0 to 75% EtOAc in hexane, to provide the title compound as a yellow solid. MS (ESI pos. ion) m/z: 436.1 (M+H).

후처리

  1. stirringThe reaction was stirred at room temperature for 5 h
  2. extractionThe aqueous solution was extracted with EtOAc (3×20 mL)
  3. concentrationThe combined EtOAc layers were concentrated in vacuo
  4. customchromatographed through a Redi-Sep® pre-packed silica gel column (12 g)
  5. washeluting with 0 to 75% EtOAc in hexane

출처 및 근거

ORD 기록
ord-9bf8c4c6da83440eb4434e110e0a4b8c
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096527B2

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