4-(Azetidin-3-yl)benzonitrile hydrochloride → US10226449, cpd 85

HRID 1487964Notes

Reaction equation

HRID 1487964 reaction equation
[NH:1]1[C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[N:3]=[C:2]1[C:11]1[C:12]([CH3:22])=[CH:13][C:14]([CH3:21])=[C:15]([CH:20]=1)[C:16](OC)=[O:17].Cl.[CH:24]1(C2C(C3NC4CCNCCC=4N=3)=CC(C(OC)=O)=C(C)C=2)CCC1.Cl.[Cl:50][C:51]1[CH:56]=[CH:55][C:54]([CH:57]2[CH2:60][NH:59][CH2:58]2)=[CH:53][CH:52]=1.Cl.N1CC(C2C=CC(C#N)=CC=2)C1>>[Cl:50][C:51]1[CH:52]=[CH:53][C:54]([CH:57]2[CH2:58][N:59]([C:16]([C:15]3[CH:20]=[C:11]([C:2]4[NH:1][C:5]5[CH2:6][CH2:7][N:8]([CH3:24])[CH2:9][CH2:10][C:4]=5[N:3]=4)[C:12]([CH3:22])=[CH:13][C:14]=3[CH3:21])=[O:17])[CH2:60]2)=[CH:55][CH:56]=1

Participants

5

Reactant 4

HCID 552549914-(Azetidin-3-yl)benzonitrile hydrochlorideHCID 717420493-(4-Chlorophenyl)azetidine--hydrogen chloride (1/1)2×HCID 90066696HCID 90066696, compound2×HCID 118250742Methyl 4-cyclobutyl-5-(1,4,5,6,7,8-hexahydroimidazo[4,5-d]azepin-2-yl)-2-methylbenzoate hydrochloride

Product 1

HCID 90030631US10226449, cpd 85

Procedure

The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of compound 82, except methyl 5-(1,4,5,6,7,8-hexahydroimidazo[4,5-d]azepin-2-yl)-2,4-dimethylbenzoate (compound 83.4) was used in place of methyl 4-cyclobutyl-5-(1,4,5,6,7,8-hexahydroimidazo[4,5-d]azepin-2-yl)-2-methylbenzoate hydrochloride (compound 82.7) and 3-(4-chlorophenyl)azetidine hydrochloride (compound 85.1) was used in place of 4-(azetidin-3-yl)benzonitrile hydrochloride (compound 5.2). m/z (ES+) 449 (M+H)+.

Sources & evidence

ORD record
ord-3abc00fa242e43a2ac3ebc24eea3873a
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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