Cesium carbonate → HCID 57590934, compound

HRID 1783770Notes

Reaction equation

[O:1]=[C:2]1[N:6]2[C:7](=[O:19])[NH:8][C:9]3[CH:10]=[C:11]4[CH:18]=[CH:17][CH:16]=[CH:15][C:12]4=[CH:13][C:14]=3[C:5]2=[N:4][N:3]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+].[C:33]([O:37][C:38](=[O:44])[NH:39][CH2:40][CH2:41][CH2:42]Br)([CH3:36])([CH3:35])[CH3:34]>CN(C=O)C>[C:33]([O:37][C:38]([NH:39][CH2:40][CH2:41][CH2:42][N:8]1[C:9]2[CH:10]=[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]3=[CH:13][C:14]=2[C:5]2=[N:4][N:3]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:2](=[O:1])[N:6]2[C:7]1=[O:19])=[O:44])([CH3:36])([CH3:35])[CH3:34]

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of tert-butyl 3,5-dioxo-5,6-dihydrobenzo[g][1,2,4]triazolo[4,3-c]quinazoline-2(3H)-carboxylate (8-6, 28 mg, 0.079 mmol, 1 equiv), cesium carbonate (100 mg, 0.31 mmol, 3.8 equiv), and N-(3-bromopropyl)carbamic acid tert-butyl ester (50 mg, 0.21 mmol, 2.6 equiv) in DMF (3 mL) was stirred at 23° C. for 16 h. The reaction mixture was filtered and the filtrate was concentrated and purified by reverse phase liquid chromatography (H2O/CH3CN gradient w/0.1% TFA present) to yield tert-butyl 6-{3-[(tert-butoxycarbonyl)amino]propyl}-3,5-dioxo-5,6-dihydrobenzo[g][1,2,4]triazolo[4,3-c]quinazoline-2(3H)-carboxylate (8-7).

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated
custompurified by reverse phase liquid chromatography (H2O/CH3CN gradient w/0.1% TFA present)

Sources & evidence

ORD record: ord-bc6f7ad8053149b7a4b6ec2cfc493544
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501435B2

Reaction notes

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