Aniline → 9-(Phenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrile

HRID 62125Notes

Reaction equation

HRID 62125 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][CH:23]=[CH:22][CH:21]=1.[K+].[Br-]>C(Cl)Cl.CCOC(C)=O>[C:20]1([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:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 253877Potassium BromideHCID 178484237HCID 178484237, compound

Product 1

HCID 904106429-(Phenylamino)thiazolo[5,4-f]quinazoline-2-carbonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Prepared from VII and aniline. Flash chromatography eluent (DCM-EtOAc, 5:5). Yield: 67%; yellow solid; mp>260° C.; IR (KBr) νmax/cm−1 3395, 3057, 2228, 1731, 1644, 1608, 1577, 1491, 1459, 1378, 1352, 1301, 1255, 1214, 1147, 1128, 1106, 1071, 967, 896, 827; 1H NMR (300 MHz, DMSO-d6) δ 8.51 (d, 1H, J=9.0 Hz), 8.11 (s, 1H), 7.78 (d, 1H, J=9.0 Hz), 7.40 (t, 2H, J=7.5 Hz), 7.20 (m, 2H), 7.11 (t, 1H, J=7.5 Hz); HRMS calcd for C16H10N5S (M+H+): 304.0657, found 304.0657.

Sources & evidence

ORD record
ord-514b5bb11f9d45089f8e7b66d0a7891c
Source dataset
uspto-grants-2016_09
Patent number
US09446044B2

Reaction notes

Loading…