Phenyl isocyanate → 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-11-yl]-N'-phenylurea Trifluoroacetate

HRID 541772Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].FC(F)(F)C(O)=O.[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[CH: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]=[C:30]([NH2:37])[CH:29]=3.[C:39]1([N:45]=[C:46]=[O:47])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[CH: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]=[C:30]([NH:37][C:46]([NH:45][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:47])[CH:29]=3

Participants

Reactant 2

HCID 7672Phenyl isocyanate

HCID 866362556-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-11-amine bis(trifluoroacetate)

Product 1

HCID 69016152N-[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-11-yl]-N'-phenylurea TrifluoroacetateYield 28%

Procedure

The desired compound was prepared according to the procedure of Example B83, using 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-11-amine bis(trifluoroacetate) and phenyl isocyanate as the starting materials in 28% yield. LCMS for C25H22ClN6O (M+H)+: m/z=457.2. 1H NMR (400 MHz, DMSO-d6): δ 9.39 (s, 1H), 9.28 (s, 1H), 8.69 (s, 1H), 8.64 (s, 1H), 8.08 (s, 1H), 7.90 (m, 1H), 7.40 (m, 2H), 7.31 (m, 1H), 7.22 (m, 3H), 7.06 (dd, 1H), 7.01 (m, 1H), 6.89 (m, 2H), 6.78 (m, 1H), 2.80 (m, 4H).

Sources & evidence

ORD record: ord-7da6543baa89463ab672d47c6437521a
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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