Benzoyl chloride, 3-chloro- → 3-Chloro-N-[6-chloro-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-yl]benzamide Hydrochloride

HRID 541763Notes

Reaction equation

HRID 541763 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[N:6][C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([CH:26]=3)[CH2:14][CH2:15][C:16]3[CH:24]=[C:20]([NH:21][C:22]=1[N:23]=2)[CH:19]=[CH:18][C:17]=3[NH2:25].[Cl:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31](Cl)=[O:32]>>[ClH:3].[Cl:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31]([NH:25][C:17]1[CH:18]=[CH:19][C:20]2[NH:21][C:22]3[N:23]=[C:7]([NH:8][C:9]4[CH:10]=[CH:11][CH:12]=[C:13]([CH:26]=4)[CH2:14][CH2:15][C:16]=1[CH:24]=2)[N:6]=[CH:5][C:4]=3[Cl:3])=[O:32]

Participants

3

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 668960506-Chloro-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-amine Dihydrochloride

Product 1

HCID 690174423-Chloro-N-[6-chloro-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-yl]benzamide HydrochlorideYield 60%

Procedure

The desired compound was prepared according to the procedure of Example B26, using 6-chloro-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-amine dihydrochloride and 3-chlorobenzoyl chloride as the starting materials in 60% yield. LCMS for C25H20Cl2N5O (M+H)+: m/z=476.3.

Sources & evidence

ORD record
ord-67c5eb520da948a5a9f4026e3349d51c
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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