1,1-Diethylguanidine → 2-Amino-8-diethylamino-4,5-dihydrothiazolo[4,5-h]quinazoline

HRID 1807650Notes

Reaction equation

CN(C)/[CH:3]=[C:4]1/[C:5](=O)[C:6]2[S:10][C:9]([N:11]=CN(C)C)=[N:8][C:7]=2[CH2:16][CH2:17]/1.[OH-].[Na+].[CH2:22]([N:24]([CH2:28][CH3:29])[C:25]([NH2:27])=[NH:26])[CH3:23]>COCCO>[NH2:11][C:9]1[S:10][C:6]2[C:5]3[N:27]=[C:25]([N:24]([CH2:28][CH3:29])[CH2:22][CH3:23])[N:26]=[CH:3][C:4]=3[CH2:17][CH2:16][C:7]=2[N:8]=1

Participants

Conditions

Temperature: 125 °C

Procedure

To N′-{6-[1-dimethylamino-meth-(E)-ylidene]-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl}-N,N-dimethyl-formamidine (Stage A.2, 1 g, 3.59 mmol) in 2-methoxyethanol (10 mL) was added NaOH (0.539 g, 13.47 mmol) and N,N-diethylguanidine (0.454 g, 3.94 mmol) under argon at rt. The RM was stirred for 3.5 h at 125° C. and then cooled to rt. After evaporation in vacuo the residue was dissolved in 0.1 M HCl (50 mL) and washed with EtOAc. The aqueous layer was then basified with 6 N NaOH and extracted 3× with EtOAc. the organic layers were dried over Na2SO4, evaporated and dried under high vacuum at 60° C. to give the title compound as orange crystals. LC: tR 3.60 min (method D). MS: M+H=276. 1H-NMR in DMSO-d6: 7.91 (s, 1H); 7.59 (s, 2H); 3.50 (q, 4H); 2.69 (dd, 4H); 1.07 (t, 6H).

Workup

temperaturecooled to rt
customAfter evaporation in vacuo the residue
dissolutionwas dissolved in 0.1 M HCl (50 mL)
washwashed with EtOAc
extractionextracted 3× with EtOAc
dry with materialthe organic layers were dried over Na2SO4
customevaporated
customdried under high vacuum at 60° C.

Sources & evidence

ORD record: ord-5c77a83ae530406da63f7c02fbacc7ed
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357707B2

Reaction notes

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