1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178510407, compound

HRID 1991942Notes

Reaction equation

HRID 1991942 reaction equation
[K+].[N:2]1([CH2:8][CH2:9][C:10]([O-:12])=O)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.C(OC(=O)CCN1CCOCC1)C.FC(F)(F)C(O)=O.[C:33]1([C:39]2[CH:44]=[C:43]([CH:45]3[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]3)[CH:42]=[CH:41][C:40]=2[NH:51][C:52]([C:54]2[NH:55][CH:56]=[C:57]([C:59]#[N:60])[N:58]=2)=[O:53])[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>O.CN(C=O)C>[C:33]1([C:39]2[CH:44]=[C:43]([CH:45]3[CH2:46][CH2:47][N:48]([C:10](=[O:12])[CH2:9][CH2:8][N:2]4[CH2:3][CH2:4][O:5][CH2:6][CH2:7]4)[CH2:49][CH2:50]3)[CH:42]=[CH:41][C:40]=2[NH:51][C:52]([C:54]2[NH:55][CH:56]=[C:57]([C:59]#[N:60])[N:58]=2)=[O:53])[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]=1

Participants

9

Reactant 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 88374Ethyl 4-morpholinepropionateHCID 68439679Potassium 3-morpholin-4-ylpropanoateHCID 1785103834-Cyano-1h-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt

Product 1

HCID 178510407HCID 178510407, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a flask containing 3-morpholin-4-yl-propionic acid potassium salt (94 mg, 0.47 mmol, prepared from 3-morpholin-4-yl-propionic acid ethyl ester exactly as described in Example 7, 4-cyano-1H-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt (179 mg, 0.36 mmol, as prepared in Example 14 (b)), EDCI (83 mg, 0.43 mmol), and HOBT (68 mg, 0.5 mmol) was added DMF (4 mL). To the stirred slurry was added DIEA (157 μL, 0.9 mmol) and the reaction was allowed to stir overnight. The reaction was diluted with H2O (10 mL) and extracted with EtOAc (2×25 mL). The combined organic extracts were dried (Na2SO4), concentrated in vacuo and the crude product was purified by silica gel preparative TLC to afford 10.4 mg (6%) of the title compound as a white solid. 1H-NMR (CDCl3; 400 MHz): δ 1.49-1.93 (m, 5H), 2.22-2.31 (m, 3H), 2.52 (br s, 4H), 2.58-2.63 (m, 3H), 2.74-2.76 (m, 4H), 3.10-3.17 (m, 2H), 3.72 (br s, 4H), 3.97-4.02 (m, 2H), 4.76-4.81 (m , 2H), 5.81-5.82 (m, 1H), 6.81-6.82 (m, 1H), 6.99-7.00 (m, 1H), 7.09-7.13 (m, 1H), 7.70 (s, 1H), 8.26 (d, 1H, J=8.2 Hz), 9.51 (s, 1H); Mass spectrum (ESI, m/z): Calcd. for C29H36N6O3, 517.28 M+H), found 517.3.

Workup

  1. extractionextracted with EtOAc (2×25 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customthe crude product was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-975192eceb074e7c8fdaf5bf9902f06a
Source dataset
uspto-grants-2010_01
Patent number
US07645755B2

Reaction notes

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