2-chloro-5-isocyanatopyridine → HCID 86636136, compound

HRID 541593Notes

Reaction equation

HRID 541593 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[CH:23][CH:24]=[C:25]([CH:46]=3)[CH2:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[CH:30][C:29]=3[NH:37][C:38]([CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)=[O:39].[Cl:47][C:48]1[CH:53]=[CH:52][C:51]([N:54]=[C:55]=[O:56])=[CH:50][N:49]=1>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[Cl:47][C:48]1[N:49]=[CH:50][C:51]([NH:54][C:55]([N:43]2[CH2:44][CH2:45][CH:40]([C:38]([NH:37][C:29]3[CH:30]=[CH:31][C:32]4[NH:33][C:34]5[N:35]=[C:19]([NH:20][C:21]6[CH:22]=[CH:23][CH:24]=[C:25]([CH:46]=6)[CH2:26][CH2:27][C:28]=3[CH:36]=4)[N:18]=[CH:17][C:16]=5[Cl:15])=[O:39])[CH2:41][CH2:42]2)=[O:56])=[CH:52][CH:53]=1

Participants

3

Reactant 2

HCID 49612732-chloro-5-isocyanatopyridineHCID 86636132N-[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]piperidine-4-carboxamide bis(trifluoroacetate)

Product 1

HCID 86636136HCID 86636136, compoundYield 23%

Procedure

The desired compound was prepared according to the procedure of Example A9, step H using 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]piperidine-4-carboxamide bis(trifluoroacetate) and 2-chloro-5-isocyanatopyridine as starting materials in 23% yield. LCMS for C30H29Cl2N8O2 (M+H)+: m/z=603.2.

Sources & evidence

ORD record
ord-8b693879db184aaa93c2e081426beacf
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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