Sodium Hydroxide → (2-Methyl-4,5-dihydro-thiazolo[4,5-h]quinazolin-8-yl)-phenyl-amine

HRID 2102793Notes

Reaction equation

[CH3:1][C:2]1[S:3][C:4]2[C:10](=O)[C:9](=[CH:12][N:13]3[CH2:18]COCC3)[CH2:8][CH2:7][C:5]=2[N:6]=1.[N+:19]([O-])(O)=O.[C:23]1([NH:29]C(N)=N)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[Na+]>COCCO>[CH3:1][C:2]1[S:3][C:4]2[C:10]3[N:19]=[C:18]([NH:29][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:13]=[CH:12][C:9]=3[CH2:8][CH2:7][C:5]=2[N:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-methyl-6-morpholin-4-ylmethylene-5,6-dihydro-4H-benzothiazol-7-one (300 mg, 1.1 mmol), N-phenyl-guanidine nitrate (449 mg, 2.3 mmol), NaOH (109 mg, 2.7 mmol) and 2-methoxyethanol (5 mL) was heated at 100° C. for 8 h. The reaction mixture was concentrated under vacuum. Flash column chromatography (20% EtOAc hexane) followed by crystallisation from EtOH afforded the title product as a white solid (154 mg, 46%): mp 223-224° C. Anal. RP-HPLC: tR 17.1 min (0-60% MeCN, purity 100%). 1H-NMR (CDCl3): δ 8.19 (s, 1H, Py-H), 7.64 (d, 2H, J 7.4, Ph-H), 7.33 (t, 2H, J 7.4, Ph-H), 7.27 (brs, 1H, NH), 7.02 (t, 1H, J 7.4, Ph-H), 3.02 (m, 4H, CH2—CH2), 2.76 (s, 3H, CH3). 13C-NMR (CDCl3): δ 169.47, 159.20, 159.10, 157.05, 155.22, 139.82, 128.96, 128.84, 122.22, 118.89, 116.57, 25.38, 24.03, 19.93. MS (ESI+): m/z 295.08 (M+H)+.

Workup

concentrationThe reaction mixture was concentrated under vacuum
customFlash column chromatography (20% EtOAc hexane) followed by crystallisation from EtOH

Sources & evidence

ORD record: ord-bcf1a40d7a734785ba2d838cc458e14f
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576091B2

Reaction notes

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