3-Methoxyphenyl isocyanate → HCID 69015662, compound

HRID 541591Notes

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][NH:43][CH2:42][CH2:41]1)=[O:39].[N:47]([C:50]1[CH:55]=[CH:54][CH:53]=[C:52]([O:56][CH3:57])[CH:51]=1)=[C:48]=[O:49]>>[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][N:43]([C:48]([NH:47][C:50]2[CH:55]=[CH:54][CH:53]=[C:52]([O:56][CH3:57])[CH:51]=2)=[O:49])[CH2:42][CH2:41]1)=[O:39]

Participants

Reactant 2

HCID 878433-Methoxyphenyl isocyanate

HCID 86636132N-[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-4-carboxamide bis(trifluoroacetate)

Product 1

HCID 69015662HCID 69015662, compoundYield 66%

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-4-carboxamide bis(trifluoroacetate) and 1-isocyanato-3-methoxybenzene as starting materials in 66% yield. 1H NMR (300 MHz, DMSO-d6): δ 9.49 (s, 1H), 9.40 (s, 1H), 9.33 (s, 1H), 8.49 (s, 1H), 8.17 (s, 1H), 7.98 (s, 1H), 7.72 (s, 1H), 7.10 (m, 5H), 6.87 (d, 1H), 6.79 (d, 1H), 6.48 (d, 1H), 4.20 (d, 2H), 3.68 (s, 3H), 2.87 (m, 6H), 2.66 (m, 1H), 1.89 (m, 2H), 1.61 (m, 2H). LCMS for C32H33ClN7O3 (M+H)+: m/z=598.2.

Sources & evidence

ORD record: ord-ffe4619621254c0c8bf1cbfcdd6cda36
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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