Potassium Bromide → 9-(3-Fluoro-4-hydroxyphenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile

HRID 62139Notes

Reaction equation

HRID 62139 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].N[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([F:27])[CH:21]=1.[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[F:27][C:22]1[CH:21]=[C:20]([NH:13][C:12]2[C:11]3[C:10](=[CH:9][CH:8]=[C:6]4[N:7]=[C:3]([C:1]#[N:2])[S:4][C:5]4=3)[N:14]=[CH:15][N:16]=2)[CH:25]=[CH:24][C:23]=1[OH:26]

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 2735918Phenol, 4-amino-2-fluoro-HCID 178484237HCID 178484237, compound

Product 1

HCID 712777389-(3-Fluoro-4-hydroxyphenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrileYield 58%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Prepared from VII and 4-amino-2-fluorophenol. Flash chromatography eluent (DCM-EtOAc, 5:5). Yield: 58%; orange solid; mp>260° C.; IR (KBr) νmax/cm−1 3375, 2228, 1731, 1649, 1619, 1578, 1512, 1470, 1373, 1347, 1292, 1241, 1204, 1150, 1111, 978, 943, 856, 836; 19F NMR (282 MHz, DMSO-d6) δ −136.8; 1H NMR (300 MHz, DMSO-d6) δ 8.46 (d, 1H, J=9.0 Hz), 8.15 (s, 1H), 7.69 (d, 1H, J=9.0 Hz), 6.97-6.81 (m, 3H); HRMS calcd for C16H9N5OSF (M+H+): 338.0512, found 338.0516.

Sources & evidence

ORD record
ord-96bd78a9f78c4247a6d092134c204076
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Reaction notes

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