5-Methylisoxazole-3-carbonyl chloride → HCID 69017667, compound

HRID 541655Notes

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:48]=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:47])[CH2:39][CH2:40][CH:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1.[CH3:49][C:50]1[O:54][N:53]=[C:52]([C:55](Cl)=[O:56])[CH:51]=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:48]=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:47])[CH2:39][CH2:40][CH:41]1[CH2:42][CH2:43][N:44]([C:55]([C:52]2[CH:51]=[C:50]([CH3:49])[O:54][N:53]=2)=[O:56])[CH2:45][CH2:46]1

Participants

Reactant 2

HCID 27368945-Methylisoxazole-3-carbonyl chloride

HCID 86636175HCID 86636175, compound

Product 1

HCID 69017667HCID 69017667, compoundYield 54%

Procedure

The desired compound was prepared according to the procedure of Example A20, 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]-3piperidin-4-ylpropanamide bis(trifluoroacetate) and 5-methylisoxazole-3-carbonyl chloride as starting materials in 54% yield. 1H NMR (300 MHz, DMSO-d6): δ 9.43 (s, 1H), 9.34 (m, 2H), 8.12 (s, 1H), 7.98 (s, 1H), 7.73 (s, 1H), 7.21 (d, 1H), 7.04 (m, 2H), 6.87 (d, 1H), 6.78 (d, 1H), 6.40 (s, 1H), 4.42 (m, 2H), 3.88 (m, 2H), 3.03 (m, 2H), 2.83 (m, 4H), 2.45 (s, 3H), 2.27 (m, 2H), 1.80 (m, 2H), 1.60 (m, 2H), 1.10 (m, 1H). LCMS for C31H33ClN7O3 (M+H)+: m/z=586.2.

Sources & evidence

ORD record: ord-d653526d204d4a6eb7ac07ca9725ccc5
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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