1,2-Dichloroethane → HCID 68927242, compound

HRID 32067Notes

Reaction equation

HRID 32067 reaction equation
Cl.Cl.[N:3]1([CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:19]=2[O:18][CH2:17][CH2:16][CH:15]3[NH2:20])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[S:31]([NH:34][CH:35]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:36][C:37](O)=[O:38])(=[O:33])=[O:32].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(Cl)CCl>C(Cl)Cl>[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[S:31]([NH:34][CH:35]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:36][C:37]([NH:20][CH:15]1[C:14]2[C:19](=[C:10]([CH2:9][N:3]3[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]3)[CH:11]=[CH:12][CH:13]=2)[O:18][CH2:17][CH2:16]1)=[O:38])(=[O:33])=[O:32]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 36326413-(naphthalene-2-sulfonamido)-3-phenylpropionic AcidHCID 689271768-Piperidin-1-ylmethylchroman-4-ylamine dihydrochloride

Product 1

HCID 68927242HCID 68927242, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Piperidin-1-ylmethylchroman-4-ylamine dihydrochloride (Step E) (28 mg, 0.11 mmol), 3-(naphthalen-2-yl-sulfonylamino)-3-phenylpropionic acid (40 mg, 0.11 mmol), HOBt (17 mg, 0.12 mmol), and DIEA (21 mg, 0.16 mmol) were dissolved in CH2Cl2 (5 mL). EDC (25 mg, 0.13 mmol) was added and the reaction was kept at 22-25° C. overnight until completed. The reaction solution was washed with dilute (˜5%) NaHCO3—H2O and H2O, then dried over MgSO4, filtered and concentrated in vacuo to provide a residue which was purified by column chromatography (silica gel, 0.5% Et3N in EtOAc). The compound was converted to the HCl salt in Et2O to provide the title compound as a mixture of diastereomers, as a white solid (ca. 1:1 by 1H NMR). MS (ESI) 584 (M+H)+.

Workup

  1. washThe reaction solution was washed
  2. additionwith dilute (˜5%) NaHCO3—H2O and H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a residue which
  7. customwas purified by column chromatography (silica gel, 0.5% Et3N in EtOAc)

Sources & evidence

ORD record
ord-621f5303f6ad4d40971dcc29cb4ee891
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

Loading…