1,2-Dichloroethane → HCID 68538958, compound

HRID 746598Notes

Reaction equation

HRID 746598 reaction equation
[Br:1][C:2]1[S:3][C:4]2[N:9]=[C:8]([C:10]([OH:12])=O)[CH2:7][C:5]=2[N:6]=1.CC[N:15](C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH4+].[Cl-]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[S:3][C:4]2[N:9]=[C:8]([C:10]([NH2:15])=[O:12])[CH2:7][C:5]=2[N:6]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 68541039HCID 68541039, compound

Product 1

HCID 68538958HCID 68538958, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add to a solution of 2-bromo-6H-pyrrolo[3,2-d]thiazole-5-carboxylic acid (2.53 gm, 10 mmol) in DMF (45 ml), DIEA (diisopropylethylamine, 10 ml, 6 eq), EDC (1-( 3-dimethylaminopropyl)-3-ethylcarbodiimide HCl, 5.0 gm, 3.5 eq); HOBT ( 1-hydroxybenzotriazole, 1.91 gm, 14 mmol, 1.4 eq) and NH4Cl (2.25 gm, 42.mmol). Stir the mixture at room temp for 6 hr and monitor by LC-MS. When complete, dilute the mixture with ethyl acetate, and wash with water and brine. Collect the solid by filtration (2.21 gm) and purify by chromatography on silica gel (ISCO silica cartridge, 4 gm, elute with methanol (10-40%) in methylene chloride) to afford the title compound (550 mg).

Workup

  1. washwash with water and brine
  2. customCollect the solid
  3. filtrationby filtration (2.21 gm)
  4. custompurify by chromatography on silica gel (ISCO silica cartridge, 4 gm, elute with methanol (10-40%) in methylene chloride)

Sources & evidence

ORD record
ord-cbd45613a38546fd8bcd13e982020613
Source dataset
uspto-grants-2008_07
Patent number
US07393867B2

Reaction notes

Loading…