3-Fluorophenyl isocyanate → HCID 69016373, compound

HRID 541783Notes

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.[F:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([N:46]=[C:47]=[O:48])[CH:41]=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:47]([NH:46][C:42]1[CH:43]=[CH:44][CH:45]=[C:40]([F:39])[CH:41]=1)=[O:48])[CH:29]=3

Participants

Reactant 2

HCID 1230643-Fluorophenyl 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 69016373HCID 69016373, compoundYield 49%

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 1-fluoro-3-isocyanatobenzene as the starting materials in 49% yield. LCMS for C25H21ClFN6O (M+H)+: m/z=475.2. 1H NMR (400 MHz, DMSO-d6): δ 9.56 (s, 1H), 9.47 (s, 1H), 9.03 (m, 1H), 8.81 (m, 1H), 8.12 (s, 1H), 7.86 (m, 1H), 7.40 (m, 1H), 7.31 (m, 1H), 7.24 (m, 2H), 7.05 (m, 3H), 6.84 (m, 2H), 6.68 (m, 1H), 2.82 (m, 4H).

Sources & evidence

ORD record: ord-0433d2ca818f4a98b918fcadd45d7c0d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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