2-Bromoacetamide → HCID 178510355, compound

HRID 1819430Notes

Reaction equation

HRID 1819430 reaction equation
Br[CH2:2][C:3]([NH2:5])=[O:4].[NH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][NH:14][C:15]2[C:20]([C:21]#[N:22])=[CH:19][N:18]=[C:17]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][C:32]([F:35])([F:34])[F:33])[N:16]=2)[CH2:9][CH2:8]1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[C:21]([C:20]1[C:15]([NH:14][CH2:13][C@H:10]2[CH2:9][CH2:8][C@H:7]([NH:6][CH2:2][C:3]([NH2:5])=[O:4])[CH2:12][CH2:11]2)=[N:16][C:17]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][C:32]([F:33])([F:34])[F:35])=[N:18][CH:19]=1)#[N:22]

Participants

6

Reactant 3

HCID 696322-BromoacetamideHCID 81531DiisopropylethylamineHCID 178510354HCID 178510354, compound

Product 1

HCID 178510355HCID 178510355, compoundYield 27.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-bromoacetamide (30 mg, 0.21 mmol), 4-{[(trans-4-aminocyclohexyl)methyl]amino}-2-{[2-(trifluoromethoxy)benzyl]amino}pyrimidine-5-carbonitrile (117 mg, 0.28 mmol) and DIPEA (74 mL, 0.43 mmol) in DMF (1 mL) was stirred at 50° C. for 4 h. The reaction mixture was then diluted with EtOAc (30 mL) and washed with water (3×3 mL) and brine. The organic phase was dried over Na2SO4 and concentrated. Silica gel preparative TLC of the crude product using 10:1:0.05 CH2Cl2:MeOH:NH4OH as an eluent afforded 28 mg (27%) of the title compound as a white solid, m/z 476.5 [M−1]+

Workup

  1. washwashed with water (3×3 mL) and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4543a444a97745c18ee25959a9e3c26d
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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