Hydrochloric Acid → HCID 11339067、化合物

HRID 1765552ノート

反応式

HRID 1765552 の反応式
Cl.Cl.CCOCC.Cl.Cl.[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21][CH2:22][N:23]([CH2:38][CH2:39][CH3:40])[CH:24]1[CH2:37][O:36][C:35]2[C:26](=[C:27]3[C:32](=[CH:33][CH:34]=2)[N:31]=[CH:30][CH:29]=[CH:28]3)[CH2:25]1>C(OCC)(=O)C>[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21][CH2:22][N:23]([CH2:38][CH2:39][CH3:40])[CH:24]1[CH2:37][O:36][C:35]2[C:26](=[C:27]3[C:32](=[CH:33][CH:34]=2)[N:31]=[CH:30][CH:29]=[CH:28]3)[CH2:25]1

参加物

5

反応物 3

HCID 313Hydrochloric Acid2 回HCID 10953452Ether hydrochlorideHCID 69497606HCID 69497606、化合物

生成物 1

HCID 11339067HCID 11339067、化合物

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To N-[3-(5-fluoro-1H-indol-3-yl)propyl]-2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-amine (example 21) (0.13 g, 0.34 mmol) in anhydrous methanol (20 mL), was added propionaldehyde (0.25 mL, 3.4 mmol), acetic acid (0.2 ml, 0.34 mmol) and sodium cyanoborohydride (0.041 g, 0.65 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with 1N NaOH, and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. Chromatography (5% MeOH/CH2Cl2) afforded 0.11 g (77%) of product as a clear oil. It was converted to the HCl salt by dissolution in ethyl acetate and addition of 1M HCl/Et2O (2.4 eq) to generate N-[3-(5-fluoro-1H-indol-3-yl)propyl]-N-propyl-2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-amine bis-hydrochloride salt as a light yellow solid: mp>148° C. MS ESI m/z 416 [M−H]−. Elemental Analysis for C26H28FN3O·2.00 HCl; Calculated: C, 63.67; H, 6.17; N, 8.57. Found: C, 63.97; H, 6.48; N, 8.28.

出典と根拠

ORDレコード
ord-cedc0cb91e5b44a29f3a0cb7ba7a0f3a
出典データセット
uspto-grants-2007_06
特許番号
US07227023B2

反応ノート

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