Sodium Hydroxide → N,N-Dimethyl-N'-(2-methyl-4,5-dihydro-thiazolo[4,5-h]quinazolin-8-yl)-benzene-1,4-diamine

HRID 2102788Notes

Reaction equation

[CH3:1][C:2]1[S:3][C:4]2[C:10](=O)[C:9](=[CH:12]N3CCOCC3)[CH2:8][CH2:7][C:5]=2[N:6]=1.[N+]([O-])(O)=O.[CH3:23][N:24]([CH3:35])[C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32]([NH2:34])=[NH:33])=[CH:27][CH:26]=1.[OH-].[Na+]>COCCO>[CH3:23][N:24]([CH3:35])[C:25]1[CH:26]=[CH:27][C:28]([NH:31][C:32]2[N:34]=[CH:12][C:9]3[CH2:8][CH2:7][C:5]4[N:6]=[C:2]([CH3:1])[S:3][C:4]=4[C:10]=3[N:33]=2)=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-methyl-6-morpholin-4-ylmethylene-5,6-dihydro-4H-benzothiazol-7-one (119 mg, 4.5 mmol), N-(4-dimethylamino-phenyl)-guanidine nitrate (137 mg, 4.5 mmol), NaOH (18 mg, 4.5 mmol), and 2-methoxyethanol (2 mL) was heated at 100° C. for 5 h. The reaction mixture was concentrated under vacuum. Flash column chromatography (20% EtOAc:hexane) gave the title product as a dark yellow solid (140 mg, 92%): mp 176-177° C. Anal. RP-HPLC: tR 11.9 min (0-60% MeCN, purity 100%). 1H-NMR (DMSO-d6): δ 9.23 (s, 1H, NH), 8.28 (s, 1H, Py-H), 7.60 (d, 2H, J 9.2, Ph-H), 6.75 (d, 2H, J 9.2, Ph-H), 3.02 (m, 4H, CH2—CH2), 2.88 (s, 6H, NMe2), 2.75 (s, 3H, CH3). 13C-NMR (DMSO-d6): δ 168.90, 159.67, 159.08, 155.77, 146.32, 131.16, 120.65, 115.25, 113.32, 41.14, 25.15, 23.45, 19.79. MS (ESI+): m/z 338.10 (M+H)+.

Workup

concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record: ord-a4992c3993e44823bcbd36afbd4498fc
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576091B2

Reaction notes

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