1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178523555, compound

HRID 1093887Notes

Reaction equation

HRID 1093887 reaction equation
CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[C:31]1([C:37]2[NH:41][N:40]=[C:39]([C:42]([NH:44][CH2:45][C:46]([OH:48])=O)=[O:43])[CH:38]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.Cl.[Cl:50][C:51]1[CH:61]=[CH:60][CH:59]=[CH:58][C:52]=1[O:53][CH:54]1[CH2:57][NH:56][CH2:55]1>CN(C=O)C>[Cl:50][C:51]1[CH:61]=[CH:60][CH:59]=[CH:58][C:52]=1[O:53][CH:54]1[CH2:57][N:56]([C:46](=[O:48])[CH2:45][NH:44][C:42]([C:39]2[CH:38]=[C:37]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[NH:41][N:40]=2)=[O:43])[CH2:55]1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 665915663-(2-Chlorophenoxy)azetidine hydrochlorideHCID 178525878HCID 178525878, compound

Product 1

HCID 178523555HCID 178523555, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIPEA (143 mg, 1.1 mmol) followed by HOBt (39 mg, 0.29 mmol) and EDCI (56 mg, 0.29 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (67 g, 0.27 mmol) in DMF (2 mL). After 2 minutes of stirring, 3-(2-chloro-phenoxy)-azetidinehydrochloride (prepared by the method used for the synthesis of Intermediate 71) (60 mg, 0.27 mmol) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was partitioned between cold water and ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. Purification by preparative HPLC afforded 48 mg (42.8% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[3-(2-chloro-phenoxy)-azetidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 411, 99.1%. 1H NMR (300 MHz, DMSO-d6): δ 13.7 (s, 1H), 8.2 (t, 1H), 7.54 (m, 2H), 7.28 (m, 5H), 7.08 (d, 1H), 7.0 (t, 1H), 6.86 (d, 1H), 5.1 (m, 1H), 4.64 (m, 1H), 4.36 (m, 1H), 4.2 (m, 1H), 3.84 (m, 3H).

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. customThe reaction mixture was partitioned between cold water and ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-c5d98a6c8c534f48b08cf86529af0170
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

Loading…