Methanesulfonyl 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-(methylsulfonyl)pyrrolidin-3-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:53]=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:52])[CH2:46][CH:47]1[CH2:51][CH2:50][NH:49][CH2:48]1.[CH3:54][S:55](Cl)(=[O:57])=[O:56]>>[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:53]=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:52])[CH2:46][CH:47]1[CH2:51][CH2:50][N:49]([S:55]([CH3:54])(=[O:57])=[O:56])[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-pyrrolidin-3-ylacetamide tris(trifluoroacetate) and methanesulfonyl chloride as starting materials in 48% yield. 1H NMR (300 MHz, DMSO-d6): δ 10.10 (s, 1H), 9.48 (s, 1H), 9.41 (s, 1H), 9.08 (s, 1H), 8.33 (s, 2H), 8.21 (s, 1H), 7.69 (s, 1H), 7.32 (d, 1H), 7.09 (d, 1H), 3.95 (s, 2H), 3.44 (m, 1H), 3.37 (m, 1H), 3.25 (m, 1H), 3.00 (m, 4H), 2.90 (s, 3H), 2.62 (m, 1H), 2.05 (m, 1H), 1.62 (m, 2H). LCMS for C24H27ClN7O3S (M+H)+: m/z=528.2.
Sources & evidence
- ORD record
- ord-6e1f44032d604dfa8ed2b862cbd8f626
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871753B2
Reaction notes
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