Sodium Hydroxide → (6-Chloro-pyridin-3-yl)-(2-methyl-4,5-dihydro-thiazolo[4,5-h]quinazolin-8-yl)-amine

HRID 2102789Notes

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.[Cl:23][C:24]1[N:29]=[CH:28][C:27]([NH:30][C:31]([NH2:33])=[NH:32])=[CH:26][CH:25]=1.[OH-].[Na+]>COCCO>[Cl:23][C:24]1[N:29]=[CH:28][C:27]([NH:30][C:31]2[N:33]=[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:32]=2)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-methyl-6-morpholin-4-ylmethylene-5,6-dihydro-4H-benzothiazol-7-one (200 mg, 0.76 mmol), N-(6-chloro-pyridin-3-yl)-guanidine nitrate (196 mg, 0.84 mmol), NaOH (34 mg, 0.84 mmol) and 2-methoxyethanol (2 mL) was heated at 100° C. for 24 h. The reaction mixture was concentrated under vacuum. Flash column chromatography (20% EtOAc:hexane) gave the pure title product as a white solid (40 mg, 16%): mp 252-253° C. Anal. RP-HPLC: tR 16.8 min (10-70% MeCN, purity 92%). 1H-NMR (DMSO-d6) δ 9.98 (s, 1H, NH), 8.90 (d, 1H, J 2.9, Ph-H), 8.44 (s, 1H, Py-H), 8.29 (dd, 1H, J 8.7, 2.4, Ph-H), 7.50 (d, 1H, J 8.7, Ph-H), 3.10 (m, 4H, CH2—CH2), 2.82 (s, 3H, CH3). 13C-NMR (DMSO-d6): δ 169.08, 159.26, 158.47, 156.22, 155.35, 141.23, 139.69, 137.05, 128.55, 127.52, 123.55, 117.05, 24.60, 23.07, 19.39. MS (ESI+): m/z 330.06 (M+H)+.

Workup

concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record: ord-9c22d4b93d294c98b2031178ce2f14c2
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576091B2

Reaction notes

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