Dimethylamine → HCID 66691742, compound

HRID 1808890Notes

Reaction equation

HRID 1808890 reaction equation
[NH2:1][C:2]1[C:3]([N+:22]([O-:24])=[O:23])=[CH:4][C:5]([Cl:21])=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:7]=1.Cl[CH2:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1.C[CH2:37][N:38](P1(N(C)CCCN1C)=NC(C)(C)C)[CH2:39]C.CNC>CN(C1C=CN=CC=1)C.C(#N)C.O>[Cl:21][C:5]1[CH:4]=[C:3]([N+:22]([O-:24])=[O:23])[C:2]([NH:1][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][C:27]([CH2:26][N:38]([CH3:39])[CH3:37])=[CH:28][CH:29]=2)=[CH:7][C:6]=1[N:8]1[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:12][CH2:13]1

Participants

8

Reactant 4

HCID 674DimethylamineHCID 701364-(Chloromethyl)benzoyl chlorideHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 22272887HCID 22272887, compound

Product 1

HCID 66691742HCID 66691742, compoundYield 58.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl 4-(5-amino-2-chloro-4-nitrophenyl)piperazine-1-carboxylate (100 mg, 0.280 mmol), 4-(chloromethyl)benzoyl chloride (106 mg, 0.561 mmol), BEMP (154 mg, 0.561 mmol), and DMAP (34 mg, 0.28 mmol) in acetonitrile (2 mL) was heated overnight at 80° C. Cooled down, treated with 0.5 ml of dimethylamine in water (40%) for 2 h. HPLC purification gave tert-butyl 4-(2-chloro-5-(4-((dimethylamino)methyl)benzamido)-4-nitrophenyl)piperazine-1-carboxylate (94 mg, 0.165 mmol).

Workup

  1. temperatureCooled down
  2. customHPLC purification

Sources & evidence

ORD record
ord-f5494afa2fcc4444ad524a727fca3674
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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