Sodium Bicarbonate → (3S,1R)-8-(3-(1-Aminoethyl)pyrrolidinyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid hydrochloride

HRID 1877

反応式

HRID 1877 の反応式
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.C([O-])(O)=O.[Na+].C(OC([NH:35][C@@H:36]([C@H:38]1[CH2:42][CH2:41][NH:40][CH2:39]1)[CH3:37])=O)(C)(C)C>C(#N)C>[ClH:18].[NH2:35][C@@H:36]([C@H:38]1[CH2:42][CH2:41][N:40]([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])[CH2:39]1)[CH3:37]

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 9927245Ethyl 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylateHCID 10104699(3S,1R)-3-(1-(t-butoxycarbonylamino)ethyl)pyrrolidine

生成物 1

HCID 512790(3S,1R)-8-(3-(1-Aminoethyl)pyrrolidinyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid hydrochloride

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A 0.44 g sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, and 1.51 g of NaHCO3 were dissolved in 40 mL of anhydrous acetonitrile, reacted with (3S,1R)-3-(1-(t-butoxycarbonylamino)ethyl)pyrrolidine (1.06 g, prepared as described by Schroeder et al., J. Heterocyclic Chem., 29:1481-1498 (1992)), and carried forward as described in Example 253k-l to give the title product. mp 235°-240° C. (dec.). MS 374 (M+H)+ ; 1H NMR (D6 -DMSO) ∂: 0.59 (m, 2H), 1.00 (m, 2H), 1.29 (d, 3H, J=6 Hz), 1.76 (m, 1H), 2.13 (m, 1H), 2.28 (m, 1H), 2.41 (m, 1H), 2.63 (s, 3H), 3.30 (m, 1H), 3.74 (m, 3H), 3.94 (m, 1H), 7.90 (s, 1H), 8.16 (br s, 3H), 9.07 (d, 1H, J=11 Hz).

出典と根拠

ORDレコード
ord-55cfd45f05674e829002cb383c59d3b6
出典データセット
uspto-grants-1998_03
特許番号
US05726182

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