3-Aminobenzonitrile → 9-(3-Cyanophenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile

HRID 62108

Reaction equation

HRID 62108 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:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[C:23]#[N:24].[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[C:23]([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:27]=[CH:26][CH:25]=1)#[N:24]

Participants

5

Reactant 3

HCID 167023-AminobenzonitrileHCID 253877Potassium BromideHCID 178484237HCID 178484237, compound

Product 1

HCID 712777349-(3-Cyanophenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrileYield 40%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Prepared from VII and 3-aminobenzonitrile. Flash chromatography eluent (DCM-EtOAc, 5:5). Yield: 40%; yellow solid; mp>260° C.; IR (KBr) νmax/cm−1 3240, 3171, 3088, 2228, 1623, 1591, 1555, 1509, 1465, 1393, 1273, 1229, 1149, 969, 919, 825; 1H NMR (300 MHz, DMSO-d6) δ 8.54 (d, 1H, J=9.0 Hz), 8.43 (s, 1H), 7.74 (m, 2H), 7.55-7.53 (m, 3H); HRMS calcd for C17H9N6S (M+H+): 329.0609, found 329.0600.

Sources & evidence

ORD record
ord-51d5cb0adfad4ced979ddfd8b807c542
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Linked notes

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