5-Amino-2-methoxyphenol → 9-(3-Hydroxy-4-methoxyphenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile

HRID 62116Notes

Reaction equation

HRID 62116 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]=[CH:22][C:23]([O:27][CH3:28])=[C:24]([OH:26])[CH:25]=1.[K+].[Br-]>CCOC(C)=O>[OH:26][C:24]1[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][C:23]=1[O:27][CH3:28]

Participants

5

Reactant 3

HCID 743145-Amino-2-methoxyphenolHCID 253877Potassium BromideHCID 178484237HCID 178484237, compound

Product 1

HCID 712777649-(3-Hydroxy-4-methoxyphenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrileYield 54%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Prepared from VII and 5-amino-2-methoxyphenol. Flash chromatography eluent (EtOAc). Yield: 54%; yellow solid; mp 248° C.; IR (KBr) νmax/cm−1 2921, 2851, 2227, 1724, 1647, 1616, 1583, 1509, 1460, 1334, 1287, 1263, 1218, 1172, 1148, 1120, 1036, 973, 953, 864, 833; 1H NMR (300 MHz, DMSO-d6) δ 8.49 (d, 1H, J=8.7 Hz), 8.05 (m, 1H), 7.77 (d, 1H, J=8.7 Hz), 7.94 (d, 2H, J=8.7 Hz), 6.65 (m, 1H), 3.77 (s, 3H); HRMS calcd for C17H12N5O2S (M+H+): 350.0712, found 350.0715.

Sources & evidence

ORD record
ord-07d9cdc1361c478eb3116d26eab44b95
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Reaction notes

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