Diisopropylethylamine → HCID 66998399, compound

HRID 559165Notes

Reaction equation

HRID 559165 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:15])[C:10]1[N:16]([CH3:29])[C:17](=[O:28])[C:18]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])=[CH:19][C:9]2=1)=[O:5].[CH2:30]([O:37][CH2:38][C:39](O)=[O:40])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.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>C(Cl)Cl>[CH2:30]([O:37][CH2:38][C:39]([NH:2][CH2:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:15])[C:10]1[N:16]([CH3:29])[C:17](=[O:28])[C:18]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])=[CH:19][C:9]2=1)=[O:5])=[O:40])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 290301(Benzyloxy)acetic acidHCID 2724699PyBOPHCID 66998027HCID 66998027, compound

Product 1

HCID 66998399HCID 66998399, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

500 mg (1.11 mmol) of 6-(aminoacetyl)-3-(2,4-dichlorophenyl)-1,9-dimethyl-1,9-dihydro-2H-pyrido[2,3-b]indol-2-one, hydrochloride described in Example 18A above, 175 μL (1.22 mmol) of benzyloxyacetic acid, 635 mg (1.22 mmol) of PyBop and 580 μL (3.33 mmol) of diisopropylethylamine are dissolved in 6 ml of CH2Cl2. The mixture is stirred at ambient temperature for 16 h. A saturated NH4CL solution is added, the mixture is then extracted with CH2CL2 and the organic phase is dried over MgSO4, filtered and concentrated under vacuum. Purification is carried out on a silica column, elution being carried out with EtOAc and then with EtOAc/5% MeOH. 454 mg of yellow crystals are obtained.

Workup

  1. additionA saturated NH4CL solution is added
  2. extractionthe mixture is then extracted with CH2CL2
  3. dry with materialthe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customPurification
  7. washis carried out on a silica column, elution

Sources & evidence

ORD record
ord-dc7144b49f034060a58dae9ce9df3461
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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