1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178427098, compound

HRID 872458Notes

Reaction equation

HRID 872458 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[NH:4][N:3]=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:40][C:41]1[CH:42]=[C:43]([C:48]2[CH:52]=[CH:51][N:50]([CH2:53][CH2:54][NH2:55])[N:49]=2)[CH:44]=[CH:45][C:46]=1[Cl:47]>C(Cl)Cl>[Cl:40][C:41]1[CH:42]=[C:43]([C:48]2[CH:52]=[CH:51][N:50]([CH2:53][CH2:54][NH:55][C:7]([C:5]3[NH:4][N:3]=[C:2]([CH3:1])[CH:6]=3)=[O:9])[N:49]=2)[CH:44]=[CH:45][C:46]=1[Cl:47]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57157163HCID 57157163, compoundHCID 178427254HCID 178427254, compound

Product 1

HCID 178427098HCID 178427098, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of 3-methyl-1H-pyrazole-5-carboxylic acid (104 mg, 0.83 mmol) in DCM (2.0 ml) was added DIPEA (0.144 mL 0.81 mmol). EDCI (159 mg, 0.83 mmol) and HOBt (112 mg, 0.83 mmol). After 10 min 2-(3-(3,4-dichloro-phenyl)-1H-pyrazol-1-yl)ethanamine (102 mg, 0.40 mmol) was added to the reaction mixture as a solution in DCM (2.0 ml). The reaction mixture was stirred at RT overnight. The reaction mixture was diluted with DCM and washed with saturated aqueous NaHCO3 solution and water. The organic phase was dried over Na2SO4, evaporated and purified by chromatography (CombiFlash, 1st column silica, eluent: 0-10% MeOH/DCM; 2nd column C-18 RP, eluent: 0-100% MeCN/water) to obtain 65 mg (45%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 2.24 (s, 3H), 3.64 (q, 2H), 4.31 (t, 2H), 6.36 (s, 1H), 6.81 (d, 1H), 7.65 (d, 1H), 7.77 (d, 1H), 7.80 (dd, 1H), 8.00 (d, 1H), 8.23 (s, 1H), 12.88 (s, 1H).

Workup

  1. washwashed with saturated aqueous NaHCO3 solution and water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated
  4. custompurified by chromatography (CombiFlash, 1st column silica, eluent: 0-10% MeOH/DCM; 2nd column C-18 RP, eluent: 0-100% MeCN/water)

Sources & evidence

ORD record
ord-5d5af9637f644da6bdee85836910f953
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…