4-Chlorobenzoyl chloride → 4-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 541764Notes

Reaction equation

HRID 541764 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:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1>>[ClH:3].[Cl:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([NH:25][C:17]2[CH:18]=[CH:19][C:20]3[NH:21][C:22]4[N:23]=[C:7]([NH:8][C:9]5[CH:10]=[CH:11][CH:12]=[C:13]([CH:26]=5)[CH2:14][CH2:15][C:16]=2[CH:24]=3)[N:6]=[CH:5][C:4]=4[Cl:3])=[O:33])=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 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 690135744-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 66%

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 4-chlorobenzoyl chloride as the starting materials in 66% yield. LCMS for C25H20Cl2N5O (M+H)+: m/z=476.2.

Sources & evidence

ORD record
ord-b4b731bb334f40539ebc3532277a7b13
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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