Hydrochloric Acid → HCID 11339067, 화합물

HRID 1765552노트

반응식

HRID 1765552 반응식
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

참가 물질

5

반응물 3

HCID 313Hydrochloric Acid2회HCID 10953452Ether hydrochlorideHCID 69497606HCID 69497606, 화합물

생성물 1

HCID 11339067HCID 11339067, 화합물

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-cedc0cb91e5b44a29f3a0cb7ba7a0f3a
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07227023B2

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