3-Methyl-1,2-oxazole-4-carboxylic acid → N-[6-Chloro-2,4,8,18,22-pentaazatetracyclo[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]-2-{1-[(3-methylisoxazol-4-yl)carbonyl]piperidin-4-yl}acetamide bis(trifluoroacetate)

HRID 541692

Reaction equation

HRID 541692 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]=[N:23][CH:24]=[C:25]([CH:47]=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](=[O:46])[CH2:39][CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.[CH3:48][C:49]1[C:53]([C:54](O)=[O:55])=[CH:52][O:51][N:50]=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:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[N:23][CH:24]=[C:25]([CH:47]=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](=[O:46])[CH2:39][CH:40]1[CH2:45][CH2:44][N:43]([C:54]([C:53]2[C:49]([CH3:48])=[N:50][O:51][CH:52]=2)=[O:55])[CH2:42][CH2:41]1

Participants

3

Reactant 2

HCID 45896923-Methyl-1,2-oxazole-4-carboxylic acidHCID 86636208N-[6-chloro-2,4,8,18,22-pentaazatetracyclo[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]-2-piperidin-4-ylacetamide bis(trifluoroacetate)

Product 1

HCID 86636213N-[6-Chloro-2,4,8,18,22-pentaazatetracyclo[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]-2-{1-[(3-methylisoxazol-4-yl)carbonyl]piperidin-4-yl}acetamide bis(trifluoroacetate)Yield 55%

Procedure

The desired compound was prepared according to the procedure of Example A27, using N-[6-chloro-2,4,8,18,22-pentaazatetracyclo[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]-2-piperidin-4-ylacetamide bis(trifluoroacetate) and 3-methylisoxazole-4-carboxylic acid as starting materials in 55% yield. LCMS for C29H30ClN8O3 (M+H)+: m/z=573.2.

Sources & evidence

ORD record
ord-3942196efeae48d39dc541e00f637723
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Linked notes

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