p-Toluidine → 9-(p-Tolylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile

HRID 62126Notes

Reaction equation

HRID 62126 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]([CH3:26])=[CH:22][CH:21]=1.[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[C:23]1([CH3:26])[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 7813p-ToluidineHCID 253877Potassium BromideHCID 178484237HCID 178484237, compound

Product 1

HCID 712777839-(p-Tolylamino)thiazolo[5,4-f]quinazoline-2-carbonitrileYield 64%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Prepared from VII and 4-toluidine. Flash chromatography eluent (DCM-EtOAc, 7:3). Yield: 64%; yellow solid; mp>260° C.; IR (KBr) νmax/cm−1 3016, 2853, 2228, 1731, 1641, 1605, 1581, 1554, 1505, 1458, 1376, 1353, 1304, 1268, 1215, 1165, 1130, 976, 831, 811; 1H NMR (300 MHz, DMSO-d6) δ 8.49 (d, 1H, J=9.0 Hz), 8.07 (s, 1H), 7.76 (d, 1H, J=9.0 Hz), 7.20-7.17 (m, 2H), 7.12-7.05 (m, 2H), 2.32 (s, 3H); HRMS calcd for C17H12N5S (M+H+): 318.0813, found 318.0811.

Sources & evidence

ORD record
ord-3fe1b9cfa3a94183ac5a08b02ce7cecf
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Reaction notes

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