Benzenamine, 3-ethynyl- → 9-(3-Ethynylphenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile

HRID 62120

Reaction equation

HRID 62120 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].[C:19]([C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)N)#[CH:20].[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[C:19]([C:21]1[CH:27]=[C:26]([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:25]=[CH:23][CH:22]=1)#[CH:20]

Participants

5

Reactant 3

HCID 104682Benzenamine, 3-ethynyl-HCID 253877Potassium BromideHCID 178484237HCID 178484237, compound

Product 1

HCID 894196789-(3-Ethynylphenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrileYield 84%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Prepared from VII and 3-ethynylaniline. Flash chromatography eluent (DCM-EtOAc, 7:3). Yield: 84%; yellow solid; mp 182° C.; IR (KBr) νmax/cm−1 3295, 3062, 2846, 2225, 1642, 1612, 1581, 1566, 1458, 1404, 1376, 1348, 1306, 1263, 1229, 1165, 1148, 1126, 971, 910, 888, 835; 1H NMR (300 MHz, DMSO-d6) δ 8.53 (d, 1H, J=8.7 Hz), 8.20 (s, 1H), 7.78 (d, 1H, J=8.7 Hz), 7.40-7.35 (m, 2H), 7.29 (m, 1H), 7.20 (m, 1H), 4.17 (s, 1H); HRMS calcd for C18H10N5S (M+H+): 328.0657, found 328.0659.

Sources & evidence

ORD record
ord-1c85c4c9c6eb4b9fa763fe27794d7813
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Linked notes

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