1,2-Dichloroethane → HCID 68934380, compound

HRID 32053Notes

Reaction equation

HRID 32053 reaction equation
[NH2:1][CH:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[S:24]([NH:27][CH:28]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:29][C:30](O)=[O:31])(=[O:26])=[O:25].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(Cl)CCl>C(Cl)Cl>[C:12]([C:8]1[CH:7]=[C:6]2[C:11]([CH:2]([NH:1][C:30](=[O:31])[CH2:29][CH:28]([NH:27][S:24]([C:15]3[CH:16]=[CH:17][C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:14]=3)(=[O:26])=[O:25])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:3][CH2:4][O:5]2)=[CH:10][CH:9]=1)#[N:13]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 36326413-(naphthalene-2-sulfonamido)-3-phenylpropionic AcidHCID 223499724-Aminochroman-7-carbonitrile

Product 1

HCID 68934380HCID 68934380, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23.5 °C

Procedure

4-Amino-chroman-7-carbonitrile (Step E) (50 mg, 0.28 mmol), 3-(naphthalen-2-ylsulfonylamino)-3-phenyl-propionic acid (100 mg, 0.28 mmol), HOBt (42 mg, 0.31 mmol), and DIEA (72 mg, 0.56 mmol) were dissolved in CH2Cl2 (10 mL). EDC (52 mg, 0.34 mmol) was added and the reaction was stirred at 22-25° C. overnight until completed. The reaction solution was washed with dilute (˜5%) NaHCO3—H2O and H2O, and solution was dried over MgSO4, filtered and concentrated in vacuo to provide a residue which was purified by column chromatography (silica gel, 25% hexane in EtOAc) to provide the title compound as a white solid mixture of diastereomers (ca. 3:2 by 1H NMR after flash column chromotography).

Workup

  1. washThe reaction solution was washed
  2. additionwith dilute (˜5%) NaHCO3—H2O and H2O, and solution
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a residue which
  7. customwas purified by column chromatography (silica gel, 25% hexane in EtOAc)
  8. customto provide

Sources & evidence

ORD record
ord-4c2016b6bd7c494fbbab0ec845cf3b29
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

Loading…