1,2-Dichloroethane → HCID 69656572, compound

HRID 857743Notes

Reaction equation

HRID 857743 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:25][CH2:24][CH2:23][C@H:19]3[C:20]([OH:22])=O)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([N:35]2[CH:39]=[N:38][CH:37]=[N:36]2)=[C:31]([CH:34]=1)[CH2:32][NH2:33].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([N:35]2[CH:39]=[N:38][CH:37]=[N:36]2)=[C:31]([CH:34]=1)[CH2:32][NH:33][C:20](=[O:22])[C@@H:19]1[CH2:23][CH2:24][CH2:25][N:18]1[C:16]([O:15][CH2:14][CH:12]1[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:17]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 688135Fmoc-Pro-OHHCID 11171817(5-Chloro-2-(1H-1,2,4-triazol-1-YL)phenyl)methanamine

Product 1

HCID 69656572HCID 69656572, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of [(9H-fluoren-9-ylmethoxy)carbonyl]-L-proline (3.23 g, 9.59 mmol), 1-[5-chloro-2-(1H-1,2,4-triazol-1-yl)phenyl]methanamine (Example 4, 2.00 g, 9.59 mmol, 1.0 equiv), EDC (2.76 g, 14.38 mmol, 1.5 equiv) and HOAt (652 mg, 4.79 mmol, 0.5 equiv) in DMF (5 mL) was brought to pH 6 by dropwise addition of Hünig's Base and stirred at room temperature for 18 h. The reaction was diluted with water and extracted into EtOAc three times. The combined organic layers were dried (anhydrous Na2SO4) and concentrated. The resulting oil was suspended and rigorously stirred in water to afford the title compound as white solid upon filtration. 1H NMR (400 MHz, CD3OD): δ 8.77 (m, 1 H), 8.24–8.22 (m, 1 H), 7.81–7.75 (m, 2 H), 7.66–7.62 (m, 2 H), 7.54–7.50 (m, 1 H), 7.45–7.31 (m, 5 H), 7.25–7.19 (m, 1 H), 4.43–4.36 (m, 2 H), 4.30–4.20 (m, 3 H), 4.05–4.02 (m, 1 H), 3.55–3.40 (m, 2 H), 2.28–2.18 (m, 1 H), 1.91–1.88 (m, 3 H). LCMS (M+H): 528.0.

Workup

  1. extractionextracted into EtOAc three times
  2. dry with materialThe combined organic layers were dried (anhydrous Na2SO4)
  3. concentrationconcentrated
  4. stirringrigorously stirred in water

Sources & evidence

ORD record
ord-c3d3712c6e774bd5a2d12f9bf7d2d876
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

Loading…