2,4-Difluoroaniline → 9-(2,4-Difluorophenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile

HRID 62138Notes

Reaction equation

HRID 62138 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]([F:27])[CH:24]=[CH:23][C:21]=1N.[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[F: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

Participants

5

Reactant 3

HCID 97092,4-DifluoroanilineHCID 253877Potassium BromideHCID 178484237HCID 178484237, compound

Product 1

HCID 712777589-(2,4-Difluorophenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrileYield 68%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Prepared from VII and 2,4-difluoroaniline. Flash chromatography eluent (DCM-EtOAc, 7:3). Yield: 68%; yellow solid; mp>260° C.; IR (KBr) νmax/cm−1 2228, 1645, 1611, 1583, 1557, 1488, 1460, 1378, 1357, 1311, 1276, 1260, 1172, 1138, 1091, 962, 854, 831, 818; 19F NMR (282 MHz, DMSO-d6) δ −117.6, −118.7; 1H NMR (300 MHz, DMSO-d6) δ 8.54 (d, 1H, J=9.0 Hz), 8.22 (s, 1H), 7.78 (d, 1H, J=9.0 Hz), 7.35-7.24 (m, 2H), 7.06 (t, 1H, J=7.8 Hz); HRMS calcd for C16H8N5SF2 (M+H+): 340.0468, found 340.0458.

Sources & evidence

ORD record
ord-ff4668994610484a9fd2b4e422dfc5ef
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Reaction notes

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