[1-(1,3,4-Thiadiazol-2-yl)piperidin-4-yl]acetic acid trifluoroacetate → 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]-2-[1-(1,3,4-thiadiazol-2-yl)piperidin-4-yl]acetamide bis(trifluoroacetate)
Reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[N:6][C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([CH:26]=3)[CH2:14][CH2:15][C:16]3[CH:24]=[C:20]([NH:21][C:22]=1[N:23]=2)[CH:19]=[CH:18][C:17]=3[NH2:25].[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30].[S:34]1[CH:38]=[N:37][N:36]=[C:35]1[N:39]1[CH2:44][CH2:43][CH:42]([CH2:45][C:46](O)=[O:47])[CH2:41][CH2:40]1>>[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30].[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30].[Cl:3][C:4]1[CH:5]=[N:6][C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([CH:26]=3)[CH2:14][CH2:15][C:16]3[CH:24]=[C:20]([NH:21][C:22]=1[N:23]=2)[CH:19]=[CH:18][C:17]=3[NH:25][C:46](=[O:47])[CH2:45][CH:42]1[CH2:43][CH2:44][N:39]([C:35]2[S:34][CH:38]=[N:37][N:36]=2)[CH2:40][CH2:41]1Participants
3
Reactant 2
Product 1
Procedure
The desired compound was prepared according to the procedure of Example A169, step B using 6-chloro2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-amine dihydrochloride and [1-(1,3,4-thiadiazol-2-yl)piperidin-4-yl]acetic acid trifluoroacetate as starting materials in 27% yield. LCMS for C27H28ClN8OS (M+H)+: m/z=547.2.
Sources & evidence
- ORD record
- ord-a7659e5412a4468899533e2431776e55
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871753B2
Reaction notes
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