Cyanogen Bromide → HCID 178512262, compound

HRID 547505Notes

Reaction equation

HRID 547505 reaction equation
[C:1]([C:4]1[CH:19]=[CH:18][C:7]([C:8]([NH:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:9])=[C:6]([NH:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=2)[N:5]=1)(=[NH:3])[NH2:2].[N:30]#[C:31]Br.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:31]([NH:3][C:1]([C:4]1[CH:19]=[CH:18][C:7]([C:8]([NH:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:9])=[C:6]([NH:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=2)[N:5]=1)=[NH:2])#[N:30]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 81531DiisopropylethylamineHCID 59738211HCID 59738211, compound

Product 1

HCID 178512262HCID 178512262, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-carbamimidoyl-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide (0.013 g, 0.034 mmol), CNBr (3N, 0.017 mL, 0.051 mmol), DIPEA (0.0085 mL, 0.051 mmol), in DCM (0.10 mL) was stirred at room temperature until the reaction was complete. The reaction mixture was concentrated to dryness and purified by RP-HPLC using a mixture of acetonitrile and H2O to give 6-(N-cyanocarbamimidoyl)-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide as a solid (0.0058 g, 41%). LC/MS (M+H+) m/z 418.1.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompurified by RP-HPLC
  3. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-c438e32e7fc74388b8f5caccd093611f
Source dataset
uspto-grants-2011_05
Patent number
US07939548B2

Reaction notes

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