Tetrafluoro-m-phenylenediamine dihydrochloride → 2,5-Bis(2-methoxy-4-(2-pyridylimino)aminophenyl)furan

HRID 49538

반응식

HRID 49538 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:14]=3[O:20][CH3:21])=[CH:11][CH:12]=2)=[C:4]([O:22][CH3:23])[CH:3]=1.[C:24]1([NH2:35])[C:29](F)=[C:28](F)[C:27](F)=[C:26]([NH2:33])C=1F.Cl.Cl>CCOC(C)=O.CCOCC>[CH3:21][O:20][C:14]1[CH:15]=[C:16]([N:19]=[N:33][C:26]2[CH:27]=[CH:28][CH:29]=[CH:24][N:35]=2)[CH:17]=[CH:18][C:13]=1[C:10]1[O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:1]=[N:33][C:26]3[CH:27]=[CH:28][CH:29]=[CH:24][N:35]=3)=[CH:3][C:4]=2[O:22][CH3:23])=[CH:12][CH:11]=1

참가 물질

4

반응물 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 104951522,5-Bis(4-amino-2-methoxyphenyl)furan

생성물 1

HCID 227188172,5-Bis(2-methoxy-4-(2-pyridylimino)aminophenyl)furan수율 75%

시약·촉매·용매 1

HCID 21584169Diethylether ethylacetate용매

실험 절차

2,5-Bis[2-methoxy-4-(2-pyridylimino)aminophenyl]furan (41, DB709) was prepared according to the procedure for 4f using diamine 3c and S-(2-naphthylmethyl)-2-pyridylthioimidate hydrobromide as starting materials. Free base: Bright yellow crystalline solid, mp 196-197° C. (EtOAc/Et2O). Yield: 75%. 1H NMR (DMSO-d6): 3.92 (s, 6H), 6.64 and 6.67 (d, 2H and s, 2H, overlapping a broad NH signal), 6.89 (s, 2H), 7.55 (dd, 2H), 7.86 (d, 2H), 7.95 (m, 2H), 8.32 (d, 2H), 8.63 (d, 2H). Dihydrochloride: brick orange solid, mp >180° C. dec. 1H NMR (DMSO-d6): 4.00 (s, 6H), 7.16 (s, 2H), 7.18 (d, 2H), 7.34 (s, 2H), 7.85 (dd, 2H), 8.13 (d, 2H), 8.22 (t, 2H), 8.49 (d, 2H), 8.89 (d, 2H), 9.39 (br s, 2H), 10.15 (br s, 2H), 11.89 (br s, 2H), MS (EI): m/z 518 (M+, 100), 414 (90.0), 371 (13.3), 310 (12.7), 267 (9.7), 155 (6.02), 104 (25.9), 77 (9.6), 43 (13.6). Anal Calcd. for C30H26N6O.2.0HCl.2.0H2O (627.51): C, H, N, Cl.

출처 및 근거

ORD 기록
ord-6740129aaa70450eb5398c0eba3700f9
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706754B2

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