Isoxazole-5-carbonyl chloride → HCID 86636176, compound
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].FC(F)(F)C(O)=O.[Cl:22][C:23]1[CH:24]=[N:25][C:26]2[NH:27][C:28]3[CH:29]=[N:30][CH:31]=[C:32]([CH:54]=3)[CH2:33][CH2:34][C:35]3[CH:43]=[C:39]([NH:40][C:41]=1[N:42]=2)[CH:38]=[CH:37][C:36]=3[NH:44][C:45](=[O:53])[CH2:46][CH:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1.[O:55]1[C:59]([C:60](Cl)=[O:61])=[CH:58][CH:57]=[N:56]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:22][C:23]1[CH:24]=[N:25][C:26]2[NH:27][C:28]3[CH:29]=[N:30][CH:31]=[C:32]([CH:54]=3)[CH2:33][CH2:34][C:35]3[CH:43]=[C:39]([NH:40][C:41]=1[N:42]=2)[CH:38]=[CH:37][C:36]=3[NH:44][C:45](=[O:53])[CH2:46][CH:47]1[CH2:52][CH2:51][N:50]([C:60]([C:59]2[O:55][N:56]=[CH:57][CH:58]=2)=[O:61])[CH2:49][CH2:48]1Participants
3
Procedure
The desired compound was prepared according to the procedure of Example A20, 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 tris(trifluoroacetate) and isoxazole-5-carbonyl chloride as starting materials in 59% yield. 1H NMR (300 MHz, DMSO-d6): δ 9.50 (d, 2H), 9.16 (s, 1H), 8.83 (s, 1H), 8.40 (s, 2H), 8.33 (s, 1H), 7.78 (s, 1H), 7.40 (d, 1H), 7.19 (d, 1H), 7.00 (s, 1H), 4.52 (m, 1H), 3.88 (m, 1H), 3.32 (m, 1H), 3.03 (s, 4H), 2.42 (m, 2H), 2.21 (m, 1H), 1.93 (m, 2H), 1.39 (m, 2H). LCMS for C28H28ClN8O3 (M+H)+: m/z=559.2.
Sources & evidence
- ORD record
- ord-ff468ecd418f4beaa5764b325e195fdb
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871753B2
Reaction notes
Loading…