Cyanogen Bromide → HCID 24752056, compound

HRID 553408Notes

Reaction equation

HRID 553408 reaction equation
[C:1]1([NH:7][CH2:8][CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.[F:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:30]Br.[N:36]#[C:37]Br>>[F:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:30][N:10]1[CH2:9][CH2:8][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:37]1=[NH:36]

Participants

5

Reactant 4

HCID 10476Cyanogen BromideHCID 742701,2-Ethanediamine, N1-phenyl-HCID 90495Di-tert-butyl dicarbonateHCID 5814364-(Bromomethyl)-1,2-difluorobenzene

Product 1

HCID 24752056HCID 24752056, compound

Procedure

The title compound was prepared from N-phenylethylenediamine in four steps by Procedure A. In the first step, one equivalent of Boc2O was used and, similarly, one equivalent of 3,4-difluorobenzyl bromide was used as benzylating reagent in the second step. After reacting with cyanogen bromide, the crude product was isolated upon aqueous work-up and purified by preparative LCMS to give the title compound as the free base. MS (ES+) m/z 288 ([M+1]+, 100); HR-MS: 288.1316 ([M+1]+, C16H16F2N3; calc. 288.131228).

Workup

  1. customthe crude product was isolated upon aqueous work-up

Sources & evidence

ORD record
ord-3260215c762641e69700eb9d1fa04003
Source dataset
uspto-grants-2011_11
Patent number
US08048877B2

Reaction notes

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