Water → HCID 66896164, compound

HRID 541742Notes

Reaction equation

HRID 541742 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:10]=[N:11][C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([CH:34]=3)[CH2:19][CH2:20][C:21]3[CH:29]=[C:25]([NH:26][C:27]=1[N:28]=2)[CH:24]=[C:23]([C:30]([O:32]C)=[O:31])[CH:22]=3.O>C(#N)C.[OH-].[Na+]>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:10]=[N:11][C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([CH:34]=3)[CH2:19][CH2:20][C:21]3[CH:29]=[C:25]([NH:26][C:27]=1[N:28]=2)[CH:24]=[C:23]([C:30]([OH:32])=[O:31])[CH:22]=3

Participants

5

Reactant 2

HCID 962WaterHCID 69015342HCID 69015342, compound

Product 1

HCID 66896164HCID 66896164, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl 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-nonaene-11-carboxylate trifluoroacetate (45 mg, 90.9 μmol) in acetonitrile (5 mL) and 2.0 M of sodium hydroxide in water (227 μL, 0.455 mmol) were stirred at 25° C. overnight. Purification by preparative LCMS gave the desired product as a white solid (16 mg, 48%). LCMS for C19H16ClN4O2 (M+H)+: m/z=367.1. 1H NMR (400 MHz, DMSO-d6): δ 9.33 (s, 1H), 9.28 (s, 1H), 8.12 (s, 1H), 8.01 (m, 1H), 7.86 (m, 1H), 7.71 (m, 1H), 7.58 (m, 1H), 7.11 (t, 1H), 6.91 (m, 1H), 6.82 (m, 1H), 2.93 (m, 2H), 2.87 (m, 2H).

Workup

  1. customPurification by preparative LCMS

Sources & evidence

ORD record
ord-c0fab17aae8240cd91bbaa132a7b2963
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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