1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57855642, compound

HRID 1177996Notes

Reaction equation

HRID 1177996 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:15]=[CH:14][C:13]([C:16]([NH:18][CH2:19][C:20]([OH:22])=O)=[O:17])=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.FC(F)(F)C(O)=O.NCC([N:61]1[CH2:66][CH2:65][N:64]([C:67](=[O:77])[C:68]2[CH:73]=[C:72]([O:74][CH3:75])[CH:71]=[CH:70][C:69]=2[Br:76])[CH:63]([CH3:78])[CH2:62]1)=O>CN(C=O)C.O>[Br:76][C:69]1[CH:70]=[CH:71][C:72]([O:74][CH3:75])=[CH:73][C:68]=1[C:67]([N:64]1[CH2:65][CH2:66][N:61]([C:20](=[O:22])[CH2:19][NH:18][C:16]([C:13]2[CH:12]=[CH:11][C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:15][CH:14]=2)=[O:17])[CH2:62][CH:63]1[CH3:78])=[O:77]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2629432-((4-Phenylphenyl)formamido)acetic acidHCID 66953688HCID 66953688, compound

Product 1

HCID 57855642HCID 57855642, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (362 mg, 0.48 mL, 2.8 mmol) was added to a stirred solution of [(Biphenyl-4-carbonyl)-amino]-acetic acid (262 mg, 1.03 mmol) in DMF (3 mL). HOBT (151.6 mg, 1.12 mmol) and EDCI (214 mg, 1.12 mmol) were then added at room temperature. After 2 minutes, 2-Amino-1-[4-(2-bromo-5-methoxy-benzoyl)-3-methyl-piperazin-1-yl]-ethanone trifluoroacetic acid salt (400 mg, 0.93 mmol) (prepared by the method described above) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid precipitated to 480 mg (93.3% yield) of biphenyl-4-carboxylic acid {2-[4-(2-bromo-5-methoxy-benzoyl)-3-methyl-piperazin-1-yl]-2-oxo-ethyl}-amide. LCMS Purity: 98.8%. 1H NMR (DMSO-d6): δ 8.5 (m, 1H), 8.0 (d, 2H), 7.8-7.7 (m, 4H), 7.6-7.4 (m, 4H), 7.0 (m, 2H), 4.75 (s, 1H), 4.4 (m, 1H), 4.2 (m, 2H), 3.8 (d, 4H), 3.2 (m, 2H), 1.4-1.1 (m, 4H).

Workup

  1. additionwas added
  2. filtrationfiltered the solid

Sources & evidence

ORD record
ord-85dca516012749da99a9af1a16410ffd
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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