Ethoxyacetic acid → HCID 66998296, compound

HRID 559153Notes

Reaction equation

HRID 559153 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[N:15]([CH3:28])[C:16](=[O:27])[C:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])=[CH:18][C:9]2=1)=[O:5].[CH2:29]([O:31][CH2:32][C:33](O)=[O:34])[CH3:30].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH4+].[Cl-]>C(Cl)Cl>[Cl:26][C:20]1[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:19]=1[C:17]1[C:16](=[O:27])[N:15]([CH3:28])[C:10]2[NH:11][C:12]3[C:8]([C:9]=2[CH:18]=1)=[CH:7][C:6]([C:4](=[O:5])[CH2:3][NH:2][C:33](=[O:34])[CH2:32][O:31][CH2:29][CH3:30])=[CH:14][CH:13]=3

Participants

7

Reactant 5

HCID 12301Ethoxyacetic acidHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 66998074HCID 66998074, compound

Product 1

HCID 66998296HCID 66998296, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

756 mg (1.73 mmol) of compound 6-(aminoacetyl)-3-(2,4-dichlorophenyl)-1-methyl-1,9-dihydro-2H-pyrido[2,3-b]indol-2-one hydrochloride from Example 5A above, 180 μl (1.90 mmol) of ethoxyacetic acid, 991 mg (1.90 mmol) of PyBOP and 905 μl (5.2 mmol) of diisopropylethylamine are dissolved in 9 ml of CH2Cl2. The mixture is stirred at ambient temperature for 16 h. A saturated solution of NH4Cl is added and the mixture is extracted with CH2Cl2, dried over MgSO4, filtered and concentrated under vacuum. The product is purified by chromatography on a silica column, elution being carried out with EtOAc and then EtOAc/3% MeOH.

Workup

  1. extractionthe mixture is extracted with CH2Cl2
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe product is purified by chromatography on a silica column, elution

Sources & evidence

ORD record
ord-95bfeb19bbba4556905449de047b63ab
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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