Acetic Acid → 3-azido-7-fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one

HRID 2223089노트

반응식

HRID 2223089 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[F:11][C:12]1[CH:13]=[CH:14][C:15]2[N:21]([CH3:22])[C:20](=[O:23])[CH2:19][N:18]=[C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:16]=2[CH:30]=1.CC(C1C=C(C(C)C)C(S([N:46]=[N+:47]=[N-:48])(=O)=O)=C(C(C)C)C=1)C.C(O)(=O)C>>[N:46]([CH:19]1[N:18]=[C:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16]2[CH:30]=[C:12]([F:11])[CH:13]=[CH:14][C:15]=2[N:21]([CH3:22])[C:20]1=[O:23])=[N+:47]=[N-:48]

참가 물질

5

반응물 4

HCID 176Acetic AcidHCID 3717072,4,6-Triisopropylbenzenesulfonyl azideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 443661797-Fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one

생성물 1

HCID 597138183-azido-7-fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one수율 83%

실험 절차

As illustrated in the scheme above and following General Procedure 6, KHMDS (1.34 mL of 0.5 M in toluene, 0.670 mmol), 7-fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one (0.171 g, 0.637 mmol), trisyl azide (0.493 g, 1.59 mmol) and acetic acid (0.16 mL, 2.8 mmol) were combined. After workup, purification of the crude product by silica gel column chromatography (100% CH2Cl2 to 9:1 CH2Cl2:EtOAc) provided the title compound as a pale yellow solid (0.163 g, 83%). 1H-NMR (CDCl3): δ 7.72-7.67 (m, 2H), 7.54-7.49 (m, 1H), 7.47-7.42 (m, 2H), 7.39 (dd, J=4.8 Hz, J=9.2 Hz, 1H), 7.36-7.30 (m, 1H), 7.08 (dd, J=2.8 Hz, J=8.4 Hz, 1H), 4.55 (s, 1H), 3.45 (s, 3H). MS (ESI) (M+H)+=310.

후처리

  1. customAfter workup, purification of the crude product by silica gel column chromatography (100% CH2Cl2 to 9:1 CH2Cl2:EtOAc)

출처 및 근거

ORD 기록
ord-858e433fb765491c822889ef18941542
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07375101B2

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