Pyridine → HCID 66897838, compound

HRID 541945Notes

Reaction equation

HRID 541945 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].F[C:9](F)(F)[C:10]([OH:12])=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:37]=3)[NH:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[CH:30][CH:29]=3.N1C=CC=CC=1.C(OC(=O)C)(=O)C>C(#N)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:10]([N:26]1[C:25]2[CH:37]=[C:21]([CH:22]=[CH:23][CH:24]=2)[NH:20][C:19]2=[N:35][C:34](=[C:16]([Cl:15])[CH:17]=[N:18]2)[NH:33][C:32]2=[CH:36][C:28](=[CH:29][CH:30]=[CH:31]2)[CH2:27]1)(=[O:12])[CH3:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86636294HCID 86636294, compound

Product 1

HCID 66897838HCID 66897838, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-chloro-2,4,8,15,22-pentaazatetracyclo[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) (10 mg, 18 μmol) in acetonitrile (0.28 mL) was treated with pyridine (7.3 μL, 91 μmol) followed by acetic anhydride (2.1 μL, 22 μmol) and stirred for 16 h. The reaction mixture was quenched with a few drops of acetic acid and purified by preparative LCMS to give the desired product (5 mg, 58%) as a solid. LCMS for C19H17ClN5O (M+H)+: m/z=366.0. 1H NMR (400 MHz, DMSO-d6): δ 9.61 (s, 1H), 9.24 (s, 1H), 8.16 (s, 1H), 8.06 (dd, J=2.0, 1.8 Hz, 1H), 7.93 (s, 1H), 7.32-7.21 (m, 4H), 7.13 (dd, J=8.2, 1.4 Hz, 1H), 6.97 (dd, J=7.8, 1.2 Hz, 1H), 4.61 (br s, 2H), 1.73 (s, 3H).

Workup

  1. customThe reaction mixture was quenched with a few drops of acetic acid
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-491e6a085f994210b6d37fe325eba24b
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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