1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178448489, compound

HRID 254651Notes

Reaction equation

HRID 254651 reaction equation
I.[CH2:2]([N:6]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[S:8][C:7]1=[NH:15])[CH2:3][CH2:4][CH3:5].[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([F:26])=[C:21]([CH:25]=1)[C:22](O)=[O:23].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:11]([C:9]1[S:8]/[C:7](=[N:15]\[C:22](=[O:23])[C:21]2[CH:25]=[C:17]([Cl:16])[CH:18]=[CH:19][C:20]=2[F:26])/[N:6]([CH2:2][CH2:3][CH2:4][CH3:5])[CH:10]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27365375-Chloro-2-fluorobenzoic acidHCID 668521773-butyl-5-tert-butyl-1,3-thiazol-2(3H)-imine hydroiodide2×

Product 1

HCID 178448489HCID 178448489, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 5-tert-butyl-3-butylthiazol-2(3H)-imine (free base of Example 6A, 500 mg, 2.4 mmol), 5-chloro-2-fluorobenzoic acid (670 mg, 2.8 mmol), EDCI (900 mg, 4.7 mmol), HOBt (635 mg, 4.7 mmol) and DMAP (36 mg, 0.3 mmol) in pyridine (20 mL) was stirred at room temperature for 2 hours. The solvent was removed, the mixture was diluted with water, and extracted with EtOAc. The organic extract was dried (Na2SO4), filtered and concentrated. The residue was triturated with EtOAc, to give 537 mg (61%) of the title compound. MS (ESI) m/z 369 (M+H)+.

Workup

  1. customThe solvent was removed
  2. additionthe mixture was diluted with water
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated with EtOAc

Sources & evidence

ORD record
ord-2d1e118698054cae87d1f2a6bd292acc
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

Loading…