3-Isocyanatobenzonitrile → HCID 86636304, compound

HRID 541963Notes

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]=[CH:23][CH:24]=[C:25]([CH:43]=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[N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.[N:44]([C:47]1[CH:48]=[C:49]([CH:52]=[CH:53][CH:54]=1)[C:50]#[N:51])=[C:45]=[O:46]>>[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]=[CH:23][CH:24]=[C:25]([CH:43]=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[N:37]1[CH2:42][CH2:41][N:40]([C:45]([NH:44][C:47]2[CH:54]=[CH:53][CH:52]=[C:49]([C:50]#[N:51])[CH:48]=2)=[O:46])[CH2:39][CH2:38]1

Participants

Reactant 2

HCID 27333153-Isocyanatobenzonitrile

HCID 86636299HCID 86636299, compound

Product 1

HCID 86636304HCID 86636304, compoundYield 35%

Procedure

The desired compound was prepared according to the procedure of Example D41 using 6-chloro-12-piperazin-1-yl-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-nonaene bis(trifluoroacetate) and 3-isocyanatobenzonitrile as the starting materials in 35% yield. LCMS for C30H28ClN8O (M+H)+: m/z=551.0. 1H NMR (300 MHz, DMSO-d6): δ 9.49 (s, 1H), 9.34 (s, 1H), 8.95 (s, 1H), 8.14 (s, 1H), 7.97-7.96 (m, 2H), 7.79-7.75 (m, 2H), 7.48-7.37 (m, 2H), 7.13-7.03 (m, 3H), 6.89-6.82 (m, 2H), 3.63 (br s, 4H), 2.99 (s, 4H), 2.84 (brs, 4H).

Sources & evidence

ORD record: ord-245f332d50694ccf9382c1677d491920
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

Loading…