Ammonium Chloride → HCID 66681377, compound

HRID 1964618Notes

Reaction equation

HRID 1964618 reaction equation
[N:1]1([C:5]([C:7]2[CH:8]=[C:9]([Cl:34])[C:10]([O:13][C:14]3[CH:15]=[C:16]([C:26]4[NH:30][C:29]([C:31]([OH:33])=O)=[CH:28][CH:27]=4)[CH:17]=[C:18]([O:20][C@@H:21]([CH3:25])[CH2:22][O:23][CH3:24])[CH:19]=3)=[N:11][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.Cl.[Cl:36][CH2:37][CH2:38][NH2:39].CCN=C=NCCCN(C)C.Cl.[Cl-].[NH4+]>ClCCl.CN(C)C1C=CN=CC=1>[N:1]1([C:5]([C:7]2[CH:8]=[C:9]([Cl:34])[C:10]([O:13][C:14]3[CH:15]=[C:16]([C:26]4[NH:30][C:29]([C:31]([NH:39][CH2:38][CH2:37][Cl:36])=[O:33])=[CH:28][CH:27]=4)[CH:17]=[C:18]([O:20][C@@H:21]([CH3:25])[CH2:22][O:23][CH3:24])[CH:19]=3)=[N:11][CH:12]=2)=[O:6])[CH2:2][CH2:3][CH2:4]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 97937372-Chloroethylamine hydrochlorideHCID 66683116HCID 66683116, compound

Product 1

HCID 66681377HCID 66681377, compoundYield 23.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

5-(3-{[5-(Azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-[(1S)-2-methoxy-1-methylethoxy]phenyl)-1H-pyrrole-2-carboxylic acid (800 mg, 1.65 mmol) synthesized in Example (71a) was dissolved in dichloromethane (10.0 mL), and 2-chloroethylamine hydrochloride (300 mg, 2.59 mmol), WSCI.HCl (630 mg, 3.29 mmol) and 4-dimethylaminopyridine (400 mg, 3.27 mmol) were added, followed by stirring at room temperature under nitrogen atmosphere for 2.5 days. To the reaction solution, a saturated aqueous ammonium chloride solution (30 mL) was added, and extraction was carried out with dichloromethane (30 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate) to afford the desired compound (210 mg, yield 23%) as a white solid.

Workup

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: ethyl acetate)

Sources & evidence

ORD record
ord-b20963c5210345f7985f93c7587d08f7
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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