2-(Isocyanatomethyl)furan → 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]-N'-(2-furylmethyl)urea 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].[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[N:23][CH:24]=[C:25]([CH:38]=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[NH2:37].[N:39]([CH2:42][C:43]1[O:44][CH:45]=[CH:46][CH:47]=1)=[C:40]=[O:41]>>[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:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[N:23][CH:24]=[C:25]([CH:38]=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:40]([NH:39][CH2:42][C:43]1[O:44][CH:45]=[CH:46][CH:47]=1)=[O:41]Participants
3
Reactant 2
Product 1
Procedure
The desired compound was prepared according to the procedure of Example B83, using 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-amine bis(trifluoroacetate) and 2-(isocyanatomethyl)furan as the starting materials in 34% yield. LCMS for C23H21ClN7O2(M+H)+: m/z=462.1. 1H NMR (400 MHz, DMSO-d6): δ 9.96 (s, 1H), 9.31 (s, 1H), 8.97 (m, 1H), 8.30 (m, 2H), 8.18 (s, 1H), 7.89 (m, 1H), 7.71 (d, 1H), 7.60 (d, 1H), 7.56 (d, 1H), 6.95-7.02 (m, 2H), 6.41 (dd, 1H), 6.28 (dd, 1H), 4.29 (d, 2H), 2.96 (m, 4H).
Sources & evidence
- ORD record
- ord-cc83a90d197e4625a8af667c2401acbd
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871753B2
Reaction notes
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