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

HRID 62131Notes

Reaction equation

HRID 62131 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].[Cl:19][C:20]1[CH:26]=[CH:25][C:23](N)=[C:22]([F:27])[CH:21]=1.[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([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)=[C:22]([F:27])[CH:21]=1

Participants

5

Reactant 3

HCID 938984-Chloro-2-fluoroanilineHCID 253877Potassium BromideHCID 178484237HCID 178484237, compound

Product 1

HCID 712777559-(4-Chloro-2-fluorophenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrileYield 56%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Prepared from VII and 4-chloro-2-fluoroaniline. Flash chromatography eluent (DCM-EtOAc, 8:2). Yield: 56%; yellow solid; mp>260° C.; IR (KBr) νmax/cm−1 2231, 1638, 1614, 1583, 1476, 1413, 1380, 1356, 1309, 1273, 1200, 1170, 1120, 982, 901, 838, 820; 1H NMR (300 MHz, DMSO-d6) δ 8.55 (d, 1H, J=9.0 Hz), 8.24 (s, 1H), 7.79 (d, 1H, J=9.0 Hz), 7.45 (d, 1H, J=9.0 Hz), 7.34 (t, 1H, J=8.4 Hz), 7.26 (d, 1H, J=9.0 Hz); HRMS calcd for C16H8N5SClF (M+H+): 356.0173, found 356.0160.

Sources & evidence

ORD record
ord-bc7010bcc2af4895a5084e04f3764055
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Reaction notes

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