4-(Trifluoromethyl)aniline → 9-(4-(Trifluoromethyl)phenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile

HRID 62140Notes

Reaction equation

HRID 62140 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]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1.[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[F:27][C:26]([F:29])([F:28])[C:23]1[CH:24]=[CH:25][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:21][CH:22]=1

Participants

5

Reactant 3

HCID 99644-(Trifluoromethyl)anilineHCID 253877Potassium BromideHCID 178484237HCID 178484237, compound

Product 1

HCID 712777719-(4-(Trifluoromethyl)phenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrileYield 61%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Prepared from VII and 4-aminobenzotrifluoride. Flash chromatography eluent (DCM-EtOAc, 7:3). Yield: 61%; yellow solid; mp>260° C.; IR (KBr) νmax/cm−1 2851, 2229, 1649, 1604, 1582, 1512, 1457, 1382, 1318, 1272, 1252, 1221, 1165, 1117, 1101, 1062, 1011, 979, 863, 830; 19F NMR (282 MHz, DMSO-d6) δ −60.01; 1H NMR (300 MHz, DMSO-d6) δ 8.53 (d, 1H, J=9.0 Hz), 8.22 (s, 1H), 7.77 (d, 1H, J=9.0 Hz), 7.70 (d, 2H, J=8.4 Hz), 7.39 (d, 2H, J=8.4 Hz); HRMS calcd for C17H9N5SF3 (M+H+): 372.0529, found 372.0535.

Sources & evidence

ORD record
ord-29ea1f39e0e043f9bd79ea3e478202f2
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Reaction notes

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