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

HRID 1714654Notes

Reaction equation

HRID 1714654 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, 1 H), 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-b2e4f486c2c24ddb936ad154f6c0033a
Source dataset
uspto-grants-2010_09
Patent number
US07795279B2

Reaction notes

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