Dichloromethane → Imidazole-1-carboxylic acid (8-tert-butyl-4,5-dihydro-thiazolo[4,5-h]quinazolin-2-yl)-amide

HRID 1807644Notes

Reaction equation

[C:1]([C:5]1[N:14]=[CH:13][C:12]2[CH2:11][CH2:10][C:9]3[N:15]=[C:16]([NH2:18])[S:17][C:8]=3[C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:19]1[N:23]=[CH:22][N:21]([C:24](N2C=NC=C2)=[O:25])[CH:20]=1.C(Cl)Cl>CN(C=O)C>[C:1]([C:5]1[N:14]=[CH:13][C:12]2[CH2:11][CH2:10][C:9]3[N:15]=[C:16]([NH:18][C:24]([N:21]4[CH:20]=[CH:19][N:23]=[CH:22]4)=[O:25])[S:17][C:8]=3[C:7]=2[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 4 °C

Procedure

8-tert-Butyl-4,5-dihydro-thiazolo[4,5-h]quinazolin-2-ylamine (Stage A.1, 0.319 g, 1.225 mmol) and CDI (278 mg, 1.715 mmol) were added to DCM (5 ml) and DMF (0.25 ml) under an argon atm. After 18 h the residue was cooled to 4° C. and the precipitate was collected by filtration. The solid was dried at 50° C. in high vacuo to give the title compound as a pale yellow solid. LCMS: tR 0.95 min and M+H 319.0 (method A2) for (8-tert-butyl-4,5-dihydro-thiazolo[4,5-h]quinazolin-2-yl)-carbamic acid methyl ester; the product of the reaction of the title compound with MeOH during the preparation of the sample as MeOH solution.

Workup

filtrationthe precipitate was collected by filtration
customThe solid was dried at 50° C. in high vacuo

Sources & evidence

ORD record: ord-f0060a546aca4b29adc7e2fed8c88a86
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357707B2

Reaction notes

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