Tert-butyl 1,4-diazepane-1-carboxylate → 4-(7-Hydroxy-6-methylquinolin-8-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 532843Notes

Reaction equation

Br[C:2]1[C:3]([O:13]C)=[C:4]([CH3:12])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[C:15]([O:19][C:20]([N:22]1[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>C(OCC)(=O)C>[C:15]([O:19][C:20]([N:22]1[CH2:28][CH2:27][CH2:26][N:25]([C:2]2[C:3]([OH:13])=[C:4]([CH3:12])[CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of product from step 2 (1.66 g, 6.58 mmol) and [1,4]Diazepane-1-carboxylic acid tert-butyl ester (4 g, 20 mmol) was heated via microwave to 140° C. for 1 h. After being cooled to rt, it was diluted with ethyl acetate, washed with saturated NaHCO3 and brine, dried over Na2SO4 and then purified by flash column chromatography on silica gel to give the desired product (0.8 g, 35%). MS (ES) m/z 358 (M+H+).

Workup

temperatureAfter being cooled to rt
washwashed with saturated NaHCO3 and brine
dry with materialdried over Na2SO4
custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record: ord-f700eea859414626adcc54878b6c11ca
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853202B2

Reaction notes

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