Reaktion #90391

ord-0e841cbaf8ad4f5cb07ff86fcefd40fd

Reaktionsgleichung

CN(C)/C=N/c1ccc2nc(C#N)sc2c1C#N
VII
CN(C)/C=N/c1ccc2nc(C#N)sc2c1C#N
(E)-N′-(2,7-dicyanobenzo[d]thiazol-6-yl)-N,N-dimethylformimidamide
Nc1ccc2c(c1)OCCO2
1,4-benzodioxan-6-amine
[Br-].[K+]
KBr
→
N#Cc1nc2ccc3ncnc(Nc4ccc5c(c4)OCCO5)c3c2s1
9-(2,3-Dihydrobenzo[b][1,4]dioxin-6-ylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile
Ausbeute 33.0%

Edukte

CN(C)/C=N/c1ccc2nc(C#N)sc2c1C#N
VII
CN(C)/C=N/c1ccc2nc(C#N)sc2c1C#N
(E)-N′-(2,7-dicyanobenzo[d]thiazol-6-yl)-N,N-dimethylformimidamide
Nc1ccc2c(c1)OCCO2
1,4-benzodioxan-6-amine
[Br-].[K+]
KBr

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O.ClCCl
DCM EtOAc

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Prepared from VII and 1,4-benzodioxan-6-amine. Flash chromatography eluent (DCM-EtOAc, 8:2). Yield: 33%; yellow solid; mp 180-190° C.; IR (KBr) νmax/cm−1 3055, 2978, 2932, 2875, 2230, 1709, 1638, 1609, 1578, 1496, 1460, 1376, 1299, 1281, 1239, 1200, 1151, 1063, 916, 885, 814; 1H NMR (300 MHz, DMSO-d6) δ 8.37 (d, 1H, J=8.4 Hz), 7.85 (m, 1H), 7.76 (m, 1H), 6.88 (d, 1H, J=8.4 Hz), 6.56 (m, 2H), 4.25 (s, 4H); HRMS calcd for C18H12N5O2S (M+H+): 362.0712, found 362.0696.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09446044B2uspto-grants-2016_09