Hydrogen Bromide → HCID 86603179, compound

HRID 1818950Notes

Reaction equation

HRID 1818950 reaction equation
Br.[NH2:2][C:3]1[S:4][C:5]([CH2:8][CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])=[CH:6][N:7]=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23]>ClCCl.CCOC(C)=O>[C:25]1([O:24][C:22](=[O:23])[NH:2][C:3]2[S:4][C:5]([CH2:8][CH2:9][N:10]3[C:18](=[O:19])[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]3=[O:20])=[CH:6][N:7]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 15891Phenyl chloroformateHCID 144238482-[2-(2-Amino-1,3-thiazol-5-yl)ethyl]-1H-isoindole-1,3(2H)-dione2×

Product 1

HCID 86603179HCID 86603179, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of a HBr salt of 2-[2-(2-amino-thiazol-5-yl)-ethyl]-isoindole-1,3-dione (compound 58.1; 1.42 mmol) in dichloromethane was added TEA (4.30 mmol) followed by the addition of phenyl chloroformate (1.43 mmol) at room temperature. After 2 hours, the reaction was concentrated to dryness to give a solid that was suspended in EtOAc, filtered, washed with additional EtOAc and dried under vacuum to provide {5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-thiazol-2-yl}-carbamic acid phenyl ester (compound 58.2, which is contaminated with triethyl amine salts) which was used in the next reaction without further purification.

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. customto give a solid
  3. filtrationfiltered
  4. washwashed with additional EtOAc
  5. customdried under vacuum

Sources & evidence

ORD record
ord-9df3f51748514daa85919b77ffbabba9
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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