5-Methylisoxazole-3-carbonyl chloride → 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-11-yl]-5-methylisoxazole-3-carboxamide Trifluoroacetate

HRID 541774Notes

Reaction equation

HRID 541774 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].FC(F)(F)C(O)=O.[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:38]=3)[CH2:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[C:30]([NH2:37])[CH:29]=3.[CH3:39][C:40]1[O:44][N:43]=[C:42]([C:45](Cl)=[O:46])[CH:41]=1>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[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:38]=3)[CH2:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[C:30]([NH:37][C:45]([C:42]1[CH:41]=[C:40]([CH3:39])[O:44][N:43]=1)=[O:46])[CH:29]=3

Participants

3

Reactant 2

HCID 27368945-Methylisoxazole-3-carbonyl chlorideHCID 866362556-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-11-amine bis(trifluoroacetate)

Product 1

HCID 69016175N-[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-11-yl]-5-methylisoxazole-3-carboxamide TrifluoroacetateYield 42%

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-11-amine bis(trifluoroacetate) and 5-methylisoxazole-3-carbonyl chloride as the starting materials in 42% yield. LCMS for C23H20ClN6O2(M+H)+: m/z=447.2. 1H NMR (400 MHz, DMSO-d6): δ 10.59 (s, 1H), 9.59 (s, 2H), 8.17 (s, 1H), 7.88 (m, 1H), 7.59 (m, 1H), 7.49 (m, 1H), 7.35 (m, 1H), 7.11 (dd, 1H), 6.89 (m, 1H), 6.84 (m, 1H), 6.64 (m, 1H), 2.88 (m, 4H), 2.48 (s, 3H).

Sources & evidence

ORD record
ord-80ce1ce03ebe4f78a9a85eb033a087c1
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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