Phenyl chloroformate → HCID 57962216, compound

HRID 541791Notes

Reaction equation

HRID 541791 reaction equation
Cl.Cl.Cl.[Cl:4][C:5]1[CH:6]=[N:7][C:8]2[NH:9][C:10]3[CH:11]=[N:12][CH:13]=[C:14]([CH:27]=3)[CH2:15][CH2:16][C:17]3[CH:25]=[C:21]([NH:22][C:23]=1[N:24]=2)[CH:20]=[CH:19][C:18]=3[NH2:26].[C:28](Cl)(=[O:36])[O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>N1C=CC=CC=1>[Cl:4][C:5]1[CH:6]=[N:7][C:8]2[NH:9][C:10]3[CH:11]=[N:12][CH:13]=[C:14]([CH:27]=3)[CH2:15][CH2:16][C:17]3[CH:25]=[C:21]([NH:22][C:23]=1[N:24]=2)[CH:20]=[CH:19][C:18]=3[NH:26][C:28](=[O:36])[O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 66896687HCID 66896687, compound

Product 1

HCID 57962216HCID 57962216, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 6-chloro-2,4,8,18,22-pentaazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-amine trihydrochloride (100.0 mg, 0.223 mmol) in pyridine (1 mL) was added carbonochloridic acid, phenyl ester (42.0 μL, 0.335 mmol). The reaction solution was stirred at room temperature overnight. The reaction solution was concentrated and diluted with water. The resulting precipitate was filtered and dried under vacuum to give the desired product (100 mg, 88%). LCMS for C24H20ClN6O2 (M+H)+: m/z=459.2.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additiondiluted with water
  3. filtrationThe resulting precipitate was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e6bc1594b841428b93cb516882cb080e
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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