2-Bromo-4-fluoroaniline → 9-(2-Bromo-4-fluorophenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile

HRID 62128

반응식

HRID 62128 반응식
[C:1]([C:3]1[S:4][C:5]2[C:11]([C:12]#[N:13])=[C:10](/[N:14]=[CH:15]/[N:16](C)C)[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].[Br:19][C:20]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:21]=1N.[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[Br:19][C:20]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:21]=1[NH:13][C:12]1[C:11]2[C:10](=[CH:9][CH:8]=[C:6]3[N:7]=[C:3]([C:1]#[N:2])[S:4][C:5]3=2)[N:14]=[CH:15][N:16]=1

참가 물질

5

반응물 3

HCID 2428732-Bromo-4-fluoroanilineHCID 253877Potassium BromideHCID 178484237HCID 178484237, 화합물

생성물 1

HCID 712777879-(2-Bromo-4-fluorophenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile수율 44%

시약·촉매·용매 1

HCID 21226138Dichloromethane ethylacetate용매

실험 절차

Prepared from VII and 2-bromo-4-fluoroaniline. Flash chromatography eluent (DCM-EtOAc, 95:5). Yield: 44%; yellow solid; mp>260° C.; IR (KBr) νmax/cm−1 3068, 2853, 2228, 1736, 1644, 1611, 1582, 1497, 1474, 1459, 1380, 1353, 1309, 1252, 1188, 1171, 1127, 1050, 1031, 980, 881, 860, 826; 19F NMR (282 MHz, DMSO-d6) δ −119.33; 1H NMR (300 MHz, DMSO-d6) δ 8.56 (d, 1H, J=9.0 Hz), 8.18 (s, 1H), 7.81 (d, 1H, J=9.0 Hz), 7.63 (d, 1H, J=7.8 Hz) 7.24-7.17 (m, 2H); HRMS calcd for C16H8N5SBrF (M+H+): 399.9668, found 399.9675.

출처 및 근거

ORD 기록
ord-d98c7de3910446d7a6a0b7d3018cd13e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446044B2

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