反応式
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]([CH2:10]O)[CH:8]=2)[S:3][N:2]=1.C(N(CC)CC)C.CS([Cl:23])(=O)=O.[NH2:24][CH:25]1[CH2:30][CH2:29][N:28]([CH2:31][C@H:32]2[C:36]3=[C:37]([F:45])[CH:38]=[N:39][C:40]4[CH:41]=[CH:42][C:43](=[O:44])[N:34]([C:35]=43)[CH2:33]2)[CH2:27][CH2:26]1.C(OC(=O)NC1CCNCC1O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.CO.ClCCl.CN(C=O)C>[ClH:23].[ClH:23].[F:45][C:37]1[CH:38]=[N:39][C:40]2[CH:41]=[CH:42][C:43](=[O:44])[N:34]3[CH2:33][C@@H:32]([CH2:31][N:28]4[CH2:27][CH2:26][CH:25]([NH:24][CH2:10][C:7]5[CH:8]=[C:9]6[N:1]=[N:2][S:3][C:4]6=[N:5][CH:6]=5)[CH2:30][CH2:29]4)[C:36]=1[C:35]=23参加物
反応物 6
HCID 8471Triethylamine
HCID 11430Potassium Carbonate
HCID 31297Methanesulfonyl chloride
HCID 21873601[1,2,3]Thiadiazolo[5,4-b]pyridin-6-ylmethanol
HCID 57525698trans-4-(Boc-amino)-3-hydroxypiperidine
HCID 68686964(4R)-4-[(4-amino-1-piperidinyl)methyl]-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one生成物 1
試薬・触媒・溶媒 4
実験手順
To a solution of [1,2,3]thiadiazolo[5,4-b]pyridin-6-ylmethanol (for a synthesis see WO2003064431, Example 1(b(iv)) (28 mg, 0.166 mmol) in THF (1 ml) was added triethylamine (0.023 ml, 0.166 mmol) and then methanesulfonyl chloride (0.013 ml, 0.166 mmol) and the reaction was then stirred at room temperature for 2 h. DMF (1 ml) was then added followed by (4R)-4-[(4-amino-1-piperidinyl)methyl]-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Enantiomer 1 (50 mg, 0.166 mmol) and potassium carbonate (0.166 mmol) and the reaction was stirred at room temperature for a further 72 h before evaporation. The residue was subjected to column chromatography on silica gel using a dichloromethane, methanol gradient to provide the free base of the title compound (20 mg, 27%).
出典と根拠
- ORDレコード
- ord-4282adf516d74e11b7fada8af21fe8a7
- 出典データセット
- uspto-grants-2010_06
- 特許番号
- US07732461B2
関連ノート
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