Isoxazole-5-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]isoxazole-5-carboxamide Trifluoroacetate

HRID 541775Notes

Reaction equation

HRID 541775 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.[O:39]1[C:43]([C:44](Cl)=[O:45])=[CH:42][CH:41]=[N:40]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:44]([C:43]1[O:39][N:40]=[CH:41][CH:42]=1)=[O:45])[CH:29]=3

Participants

3

Reactant 2

HCID 2736707Isoxazole-5-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 69016902N-[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]isoxazole-5-carboxamide TrifluoroacetateYield 45%

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 isoxazole-5-carbonyl chloride as the starting materials in 45% yield. LCMS for C22H18ClN6O2(M+H)+: m/z=433.1. 1H NMR (400 MHz, DMSO-d6): δ 10.65 (s, 1H), 9.52 (s, 1H), 9.49 (s, 1H), 8.75 (d, 1H), 8.12 (s, 1H), 7.84 (m, 1H), 7.56 (m, 1H), 7.48 (m, 1H), 7.27 (m, 1H), 7.20 (d, 1H), 7.06 (dd, 1H), 6.85 (m, 1H), 6.82 (m, 1H), 2.84 (m, 4H).

Sources & evidence

ORD record
ord-7dc2da9b985a4611ae53f55a9f9949a7
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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