1,2-Dichloroethane → HCID 68538958, compound

HRID 1993798Notes

Reaction equation

HRID 1993798 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, 42.0 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-e58e9088a2864d6e8a7b2ad211238fad
Source dataset
uspto-grants-2010_01
Patent number
US07652046B2

Reaction notes

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