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

HRID 532843
Notes
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Reaction equation

HRID 532843 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 593661888-Bromo-7-methoxy-6-methylquinoline

Product 1

HCID 1359972734-(7-Hydroxy-6-methylquinolin-8-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl esterYield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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

  1. temperatureAfter being cooled to rt
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes