Pyrrolidine → 8-(3-(1-amino-1-methylethyl)pyrrolidinyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic Acid Hydrochloride

HRID 1450086

반응식

HRID 1450086 반응식
C([O:3][C:4]([C:6]1[C:15](=[O:16])[N:14]2[C:9]([C:10]([CH3:19])=[C:11]([Cl:18])[C:12]([F:17])=[CH:13]2)=[C:8]([CH:20]2[CH2:22][CH2:21]2)[CH:7]=1)=[O:5])C.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>C(#N)C>[ClH:18].[NH2:14][C:9]([CH:25]1[CH2:26][CH2:27][N:23]([C:11]2[C:12]([F:17])=[CH:13][N:14]3[C:9]([C:10]=2[CH3:19])=[C:8]([CH:20]2[CH2:21][CH2:22]2)[CH:7]=[C:6]([C:4]([OH:3])=[O:5])[C:15]3=[O:16])[CH2:24]1)([CH3:10])[CH3:8]

참가 물질

4

반응물 2

HCID 31268PyrrolidineHCID 9927245Ethyl 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate

생성물 1

HCID 5127898-(3-(1-amino-1-methylethyl)pyrrolidinyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic Acid Hydrochloride

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A 150 mg sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, was dissolved in 2 mL of anhydrous acetonitrile, reacted with 1-amino-1-methylethyl)pyrrolidine (155 mg, 0.77 mmol, prepared by standard method from the free base described by Hayakawa et al., U.S. Pat. No. 5,098,912, issued Mar. 24, 1992), and carded forward as described in Example 253k-1 to give the title product. MS (high resolution) found: 388.2047; calc: 388.2036 (M+H)+ ; 1H NMR (D6 -DMSO) δ:0.60 (m, 2H), 0.94 (m, 1H), 1.07 (m, 1H), 1.33 (s, 3H), 1.34 (s, 1H), 2.83 (m, 1H), 2.07 (m, 1H), 2.19 (m, 2H), 2.63 (s, 3H), 3.60 (b t, 1H), 3.68 (b t, 1H), 3.81 (m, 1H), 3.93 (m, 1H), 7.90 (s, 1H), 8.11 (b s, 1H), 9.08 (d, 1H), 13.83 (b s, 1Calcd for C21H27N3O3FCl.5 H2O:C, 55.93; H, 6.71; N, 9.32; Found: C, 56.07; H, 6.71; N, 8.95.

후처리

  1. customprepared by standard method from the free base

출처 및 근거

ORD 기록
ord-95ef711af9364cf9a873f0d208f5d0d7
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05599816

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