N-bromobutanimide → HCID 46917419, compound

HRID 1619090Notes

Reaction equation

HRID 1619090 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([C:14]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([C:32](=[O:44])[NH:33][C:34]4[C:39]([CH2:40][CH3:41])=[CH:38][CH:37]=[CH:36][C:35]=4[CH2:42][CH3:43])=[CH:28][C:27]=3[CH3:45])[N:20]=2)[N:16]([CH3:46])[CH:15]=1)=[O:13])[CH3:2].C1C(=O)N([Br:54])C(=O)C1>CN(C=O)C.CCOC(C)=O>[CH2:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[NH:11][C:12]([C:14]1[CH:18]=[C:17]([C:19]2[C:24]([Br:54])=[CH:23][N:22]=[C:21]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([C:32](=[O:44])[NH:33][C:34]4[C:39]([CH2:40][CH3:41])=[CH:38][CH:37]=[CH:36][C:35]=4[CH2:42][CH3:43])=[CH:28][C:27]=3[CH3:45])[N:20]=2)[N:16]([CH3:46])[CH:15]=1)=[O:13])[CH3:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 46917346HCID 46917346, compound

Product 1

HCID 46917419HCID 46917419, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-{2-[4-(2,6-diethyl-phenylcarbamoyl)-2-methyl-phenylamino]-pyrimidin-4-yl}-1-methyl-1H-pyrrole-3-carboxylic acid (2,6-diethyl-phenyl)-amide (100 mg, 0.1626 mmol) and NBS (29 mg, 0.1626 mmol) in 7.5 mL of DMF was stirred at room temperature for 1 h. The mixture was then diluted with AcOEt and washed with water. The organic layer was dried over Na2SO4 and the solvent removed under reduced pressure. The target product was purified by preparative HPLC (39.8 mg, 35%, Exact Mass: calculated 693.2547, found 693.2548) as well as 2-bromo-5-{2-[4-(2,6-diethyl-phenylcarbamoyl)-2-methyl-phenylamino]-pyrimidin-4-yl}-1-methyl-1H-pyrrole-3-carboxylic acid (2,6-diethyl-phenyl)-amide (24.7 mg, 22%, Exact Mass: calculated 693.2547, found 693.2556.) and 2-bromo-5-{5-bromo-2-[4-(2,6-diethyl-phenylcarbamoyl)-2-methyl-phenylamino]-pyrimidin-4-yl}-1-methyl-1H-pyrrole-3-carboxylic acid (2,6-diethyl-phenyl)-amide (8.1 mg, 6.5%, Exact Mass: calculated 771.1652, found 771.1653).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent removed under reduced pressure
  4. customThe target product was purified by preparative HPLC (39.8 mg, 35%, Exact Mass: calculated 693.2547, found 693.2548) as well as 2-bromo-5-{2-[4-(2,6-diethyl-phenylcarbamoyl)-2-methyl-phenylamino]-pyrimidin-4-yl}-1-methyl-1H-pyrrole-3-carboxylic acid (2,6-diethyl-phenyl)-amide (24.7 mg, 22%, Exact Mass: calculated 693.2547, found 693.2556.) and 2-bromo-5-{5-bromo-2-[4-(2,6-diethyl-phenylcarbamoyl)-2-methyl-phenylamino]-pyrimidin-4-yl}-1-methyl-1H-pyrrole-3-carboxylic acid (2,6-diethyl-phenyl)-amide (8.1 mg, 6.5%, Exact Mass: calculated 771.1652, found 771.1653)

Sources & evidence

ORD record
ord-e40859dd6daa4e8084156e1a2a97ba83
Source dataset
uspto-grants-2014_07
Patent number
US08772280B2

Reaction notes

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