Phenyl isocyanate → HCID 69015428, compound

HRID 541600Notes

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:46]=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:38]([CH:40]1[CH2:45][CH2:44][CH2:43][NH:42][CH2:41]1)=[O:39].[C:47]1([N:53]=[C:54]=[O:55])[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=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:46]=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:38]([CH:40]1[CH2:45][CH2:44][CH2:43][N:42]([C:54]([NH:53][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:55])[CH2:41]1)=[O:39]

Participants

Reactant 2

HCID 7672Phenyl isocyanate

HCID 86636139HCID 86636139, compound

Product 1

HCID 69015428HCID 69015428, compoundYield 42%

Procedure

The desired compound was prepared according to the procedure of Example A9, step H using 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]piperidine-3-carboxamide bis(trifluoroacetate) and phenyl isocyanate as starting materials in 42% yield. 1H NMR (300 MHz, DMSO-d6): δ 9.43 (s, 1H), 9.40 (s, 1H), 9.38 (s, 1H), 8.59 (s, 1H), 8.14 (s, 1H), 8.00 (s, 1H), 7.72 (s, 1H), 7.44 (d, 2H), 7.21 (m, 3H), 7.04 (m, 2H), 6.90 (m, 2H), 4.22 (d, 1H), 4.10 (d, 1H), 2.90 (m, 6H), 2.63 (m, 1H), 2.03 (m, 1H), 1.72 (m, 2H), 1.47 (m, 1H). LCMS for C31H31ClN7O2 (M+H)+: m/z=568.2.

Sources & evidence

ORD record: ord-4f3c60e6e701417f99dd4b9df2c2b0bc
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

Loading…