1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66934364, compound

HRID 1365506Notes

Reaction equation

HRID 1365506 reaction equation
[NH2:1][C@:2]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=1)([C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([F:17])[CH:8]=1)[CH2:3][C:4](O)=[O:5].CC[N:27]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH4+].[Cl-]>ClCCCl.C(Cl)Cl>[NH2:1][C@:2]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=1)([C:7]1[CH:12]=[C:11]([C:13]([F:15])([F:16])[F:14])[CH:10]=[C:9]([F:17])[CH:8]=1)[CH2:3][C:4]([NH2:27])=[O:5]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 58921171HCID 58921171, compound

Product 1

HCID 66934364HCID 66934364, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

(S)-3-amino-3-(5-chloropyridin-2-yl)-3-(3-fluoro-5-(trifluoromethyl)phenyl)propanoic acid (0.047 g, 0.13 mmol, prepared as described in Procedure 29) was dissolved in DCE (5 mL) at room temperature. To the solution was added EDCI (0.035 g, 0.14 mmol), HOBt (0.025 mg, 0.14 mmol), NH4Cl (0.075 g, 1.3 mmol) and TEA (ca.0.070 g). The resulting solution was stirred for 18 h then heated to 50° C. for 8 h. On cooling the reaction mixture was diluted with DCM (ca. 10 mL) and washed with saturated NaCl solution (ca.2×10 mL). (S)-3-amino-3-(5-chloropyridin-2-yl)-3-(3-fluoro-5-(trifluoromethyl)phenyl) propanamide was isolated as a colorless oil (0.03 lg, 65% yield) and was used without further purification. LCMS: 1.25 min [M+1] 362.2 (2 min gradient, MeOH/H2O 0.1% TFA).

Workup

  1. temperatureOn cooling the reaction mixture
  2. washwashed with saturated NaCl solution (ca.2×10 mL)

Sources & evidence

ORD record
ord-2aaff2f95b00453fb4a73715382b97f1
Source dataset
uspto-grants-2011_02
Patent number
US07888376B2

Reaction notes

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