3,4,7,8-Tetramethyl-1,10-phenanthroline → 6-({1-[(4-Cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-yl}oxy)-2-methylquinoline

HRID 2361659Notes

Reaction equation

HRID 2361659 reaction equation
CC1C=NC2C(C=1C)=CC=C1C=2N=CC(C)=C1C.[CH:19]1([N:23]2[CH2:29][CH2:28][CH2:27][N:26]([C:30]([N:32]3[CH2:35][CH:34]([OH:36])[CH2:33]3)=[O:31])[CH2:25][CH2:24]2)[CH2:22][CH2:21][CH2:20]1.Br[C:38]1[CH:39]=[C:40]2[C:45](=[CH:46][CH:47]=1)[N:44]=[C:43]([CH3:48])[CH:42]=[CH:41]2>>[CH:19]1([N:23]2[CH2:29][CH2:28][CH2:27][N:26]([C:30]([N:32]3[CH2:33][CH:34]([O:36][C:38]4[CH:39]=[C:40]5[C:45](=[CH:46][CH:47]=4)[N:44]=[C:43]([CH3:48])[CH:42]=[CH:41]5)[CH2:35]3)=[O:31])[CH2:25][CH2:24]2)[CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 3

HCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 5228856-Bromo-2-methylquinolineHCID 44462713HCID 44462713, compound

Product 1

HCID 444771626-({1-[(4-Cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-yl}oxy)-2-methylquinoline

Procedure

In a similar fashion (Route 21, GP J) except for replacing phenantroline with 3,4,7,8-tetramethylphenantroline, 1-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-ol (128 mg, 0.51 mmol) and 6-bromo-2-methylquinoline (224 mg, 1.01 mmol) gave the title compound as brown oil after purification by FCC (52 mg, 25%).

Sources & evidence

ORD record
ord-16eda6def6d7498c878e880d35de9223
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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