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

HRID 538792Notes

Reaction equation

HRID 538792 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-f2ddfc802f624721ab98bcc4aaa1a8ac
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

Loading…