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P-Anisidine → 9-(4-Methoxyphenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile

HRID 62109
Notes
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Reaction equation

HRID 62109 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].[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24](N)=[CH:23][CH:22]=1.[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([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:23][CH:22]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 253877Potassium BromideHCID 178484237HCID 178484237, compound

Product 1

HCID 712777629-(4-Methoxyphenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrileYield 20%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Prepared from VII and 4-methoxyaniline. Flash chromatography eluent (DCM-EtOAc, 8:2). Yield: 20%; orange solid, mp>260° C.; IR (KBr) νmax/cm−1 3346, 2977, 2361, 2227, 1644, 1609, 1581, 1503, 1460, 1377, 1354, 1303, 1239, 1164, 1129, 1051, 1032, 975, 829; 1H NMR (300 MHz, DMSO-d6) δ 8.44 (s, 1H), 7.95 (d, 1H, J=9.0 Hz), 7.70 (d, 1H, J=9.0 Hz), 7.45 (d, 2H, J=9.0 Hz), 6.99 (d, 2H, J=9.0 Hz), 3.76 (s, 3H); HRMS calcd for C17H12N5OS (M+H+): 334.0763, found 334.0758.

Sources & evidence

ORD record
ord-c9828695b9fc4aa999a3e2662af7e9c2
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09446044B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes