Dimethylsulphamoyl chloride → 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-[(dimethylamino)sulfonyl]piperidin-4-yl}acetamide bis(trifluoroacetate)
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.[CH3:55][N:56]([CH3:61])[S:57](Cl)(=[O:59])=[O:58]>>[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]([S:57]([N:56]([CH3:61])[CH3:55])(=[O:59])=[O:58])[CH2:49][CH2:48]1Participants
3
Reactant 2
Product 1
Procedure
The desired compound was prepared according to the procedure of Example A42, 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 dimethylsulfamoyl chloride as starting materials in 48% yield. 1H NMR (300 MHz, DMSO-d6): δ 10.02 (s, 1H), 9.40 (m, 2H), 9.02 (s, 1H), 8.31 (m, 2H), 8.21 (s, 1H), 7.68 (m, 1H), 7.30 (m, 1H), 7.07 (m, 1H), 3.58 (m, 2H), 2.99 (m, 4H), 2.85 (m, 2H), 2.72 (s, 6H), 2.32 (m, 2H), 1.91 (m, 1H), 1.77 (m, 2H), 1.25 (m, 2H). LCMS for C26H32ClN8O3S (M+H)+: m/z=571.2.
Sources & evidence
- ORD record
- ord-4bad6dee00cc4babbc935ab3ef66b7d1
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871753B2
Reaction notes
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