Azetidine → Methyl 3-(2-(2-(azetidin-1-yl)ethyl)-1H-imidazol-5-yl)-4-methylbenzoate

HRID 1488008Notes

Reaction equation

HRID 1488008 reaction equation
ClCCC1NC(C2C=C(C=CC=2C)C([N:15]2[CH2:20][CH2:19][CH:18](C3C=CC(C#N)=CC=3)CC2)=O)=C(C)N=1.O[CH2:34][CH2:35][C:36]1[NH:37][C:38]([C:41]2[CH:42]=[C:43]([CH:48]=[CH:49][C:50]=2[CH3:51])[C:44]([O:46][CH3:47])=[O:45])=[CH:39][N:40]=1.OCCC1NC(C2C=C(C=CC=2C)C(N2CCC(C3C=CC(C#N)=CC=3)CC2)=O)=C(C)N=1.N1CCC1>>[N:15]1([CH2:34][CH2:35][C:36]2[NH:37][C:38]([C:41]3[CH:42]=[C:43]([CH:48]=[CH:49][C:50]=3[CH3:51])[C:44]([O:46][CH3:47])=[O:45])=[CH:39][N:40]=2)[CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 4

HCID 10422AzetidineHCID 90030129Methyl 3-(2-(2-hydroxyethyl)-1H-imidazol-5-yl)-4-methylbenzoate2×HCID 1784258004-(1-(3-(2-(2-Chloroethyl)-4-methyl-1H-imidazol-5-yl)-4-methylbenzoyl)piperidin-4-yl)benzonitrileHCID 1784258034-(1-(3-(2-(2-hydroxyethyl)-4-methyl-1H-imidazol-5-yl)-4-methylbenzoyl)piperidin-4-yl)benzonitrile

Product 1

HCID 90030616Methyl 3-(2-(2-(azetidin-1-yl)ethyl)-1H-imidazol-5-yl)-4-methylbenzoate

Procedure

The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of compounds 24.1 and 24, except methyl 3-(2-(2-hydroxyethyl)-1H-imidazol-5-yl)-4-methylbenzoate (compound 157.1) was used in place of 4-(1-(3-(2-(2-hydroxyethyl)-4-methyl-1H-imidazol-5-yl)-4-methylbenzoyl)piperidin-4-yl)benzonitrile (compound 23) and azetidine was used in place of dimethylamine.

Sources & evidence

ORD record
ord-eea22f87aab74b1b99118b43b078a225
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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