1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178453786, compound

HRID 2367805Notes

Reaction equation

HRID 2367805 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.FC(F)(F)C(O)=O.[C:50]1([C:56]2[CH:61]=[C:60]([CH:62]3[CH2:67][CH2:66][NH:65][CH2:64][CH2:63]3)[CH:59]=[CH:58][C:57]=2[NH:68][C:69]([C:71]2[NH:72][CH:73]=[C:74]([C:76]#[N:77])[N:75]=2)=[O:70])[CH2:55][CH2:54][CH2:53][CH2:52][CH:51]=1>C(Cl)Cl>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][C:10]([N:65]1[CH2:66][CH2:67][CH:62]([C:60]2[CH:59]=[CH:58][C:57]([NH:68][C:69]([C:71]3[NH:72][CH:73]=[C:74]([C:76]#[N:77])[N:75]=3)=[O:70])=[C:56]([C:50]3[CH2:55][CH2:54][CH2:53][CH2:52][CH:51]=3)[CH:61]=2)[CH2:63][CH2:64]1)=[O:12])([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 1785103834-Cyano-1h-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt

Product 1

HCID 178453786HCID 178453786, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-BOC-glycine (0.29 g, 1.63 mmol) in CH2Cl2 (10 mL) was treated with DIEA (0.85 mL, 4.90 mmol), HOBt (0.26 g, 1.96 mmol), and EDCI (0.38 g, 1.96 mmol). The mixture was stirred at room temperature for 10 min and added to a suspension of 4-cyano-1H-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt (as prepared in Example 14, step (b), 0.80 g, 1.63 mmol) in CH2Cl2 (20 mL). The solution was stirred at room temperature for 17 h. Solvents were evaporated in vacuo. Silica gel chromatography (50% EtOAc in hexanes) afforded the title compound (0.41 g, 47%) as a white solid. 1H-NMR (CDCl3; 400 MHz): δ 9.53 (s, 1H), 8.26 (d, 1H, J=8.4 Hz), 7.80-7.78 (m, 1H), 7.71 (s, 1H), 7.45-7.43 (m, 1H), 7.06 (d, 1H, J=8.4 Hz), 7.00 (s, 1H), 5.83 (br s, 1H), 5.76 (br s, 1H), 4.78-4.68 (m, 1H), 3.96-3.85 (m, 2H), 3.17-3.03 (m, 1H), 2.78-2.63 (m, 2H), 2.29 (br s, 2H), 2.22 (br s, 2H), 1.95-1.87 (m, 2H), 1.86-1.72 (m, 4H), 1.70-1.55 (m, 2H), 1.44 (s, 9H). LC-MS (ESI, m/z): Calcd. for C29H36N6O4 533.3 (M+H). found 532.9.

Workup

  1. stirringThe solution was stirred at room temperature for 17 h
  2. customSolvents were evaporated in vacuo

Sources & evidence

ORD record
ord-65f901da67664d949400ff04c317f4ec
Source dataset
uspto-grants-2014_04
Patent number
US08697716B2

Reaction notes

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