Hydrochloric Acid → HCID 22144680, compound

HRID 1825009Notes

Reaction equation

HRID 1825009 reaction equation
[CH3:1][C:2]([CH3:37])([CH3:36])[CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23])[C:11]([C:24]([NH:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30](O)=[O:31])=[O:25])=[CH:10]2)=[O:5].CN(C)CCCN=C=NCC.Cl.[C:50]([NH2:54])([CH3:53])([CH3:52])[CH3:51]>CN(C)C1C=CN=CC=1.ClCCl>[C:50]([NH:54][C:30]([C:29]1[CH:28]=[C:27]([NH:26][C:24]([C:11]2[N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])[C:13]3[C:9]([CH:10]=2)=[CH:8][C:7]([NH:6][C:4](=[O:5])[CH2:3][C:2]([CH3:36])([CH3:1])[CH3:37])=[CH:15][CH:14]=3)=[O:25])[CH:35]=[CH:34][CH:33]=1)=[O:31])([CH3:53])([CH3:52])[CH3:51]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6385Tert-ButylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 22144645HCID 22144645, compound

Product 1

HCID 22144680HCID 22144680, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

20 mg (0.04 mmol) of the compound from Example 64, 11.5 mg (0.06 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide×HCl and 2.5 mg (0.02 mmol) of 4-dimethylaminopyridine are initially charged in 1 ml of dichloromethane. 3.5 mg (0.05 mmol) of tert-butylamine are added, and the mixture is stirred at RT overnight. For work-up, the mixture is diluted and extracted with aqueous hydrochloric acid and dichloromethane. The organic phase is washed with sat. sodium chloride solution, dried with sodium sulphate, filtered and dried under reduced pressure. Purification is carried out by chromatography on silica gel.

Workup

  1. additionFor work-up, the mixture is diluted
  2. extractionextracted with aqueous hydrochloric acid and dichloromethane
  3. washThe organic phase is washed with sat. sodium chloride solution
  4. dry with materialdried with sodium sulphate
  5. filtrationfiltered
  6. customdried under reduced pressure
  7. customPurification

Sources & evidence

ORD record
ord-e4b8b004f3c14a22a1c9f53b22c7fdbb
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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