Potassium Bromide → 9-(2-Fluoro-4-methoxyphenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile

HRID 62129Notes

Reaction equation

HRID 62129 reaction equation
[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].[F:19][C:20]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:21]=1N.[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[F:19][C:20]1[CH:26]=[C:25]([O:27][CH3:28])[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

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 37563832-Fluoro-4-methoxyanilineHCID 178484237HCID 178484237, compound

Product 1

HCID 712777789-(2-Fluoro-4-methoxyphenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrileYield 85%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Prepared from VII and 2-fluoro-4-methoxyaniline. Flash chromatography eluent (DCM-EtOAc, 5:5). Yield: 85%; yellow solid; mp>260° C.; IR (KBr) νmax/cm−1 2844, 2226, 1731, 1649, 1613, 1583, 1507, 1493, 1460, 1445, 1379, 1356, 1305, 1263, 1212, 1168, 1153, 1129, 1090, 1027, 980, 947, 841, 830, 818; 19F NMR (282 MHz, DMSO-d6) δ −120.02; 1H NMR (300 MHz, DMSO-d6) δ 8.51 (d, 1H, J=9.0 Hz), 8.15 (s, 1H), 7.77 (d, 1H, J=9.0 Hz), 7.30 (s, 1H), 6.92 (m, 1H), 6.80 (d, 2H, J=9.0 Hz); HRMS calcd for C17H11N5OSF (M+H+): 352.0668, found 352.0658.

Sources & evidence

ORD record
ord-e4e17aee01ea4d63bcfbcce3a99bca56
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Reaction notes

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