Bromoacetyl bromide → 5-chloro-thiophene-2-carboxylic acid [(R)-1-(2-bromo-acetyl)-pyrrolidin-3-yl]-amide

HRID 1162613Notes

Reaction equation

HRID 1162613 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][C@@H:4]([NH:7][C:8]([C:10]2[S:11][C:12]([Cl:15])=[CH:13][CH:14]=2)=[O:9])[CH2:3]1.[Br:16][CH2:17][C:18](Br)=[O:19]>C1COCC1>[Br:16][CH2:17][C:18]([N:2]1[CH2:6][CH2:5][C@@H:4]([NH:7][C:8]([C:10]2[S:11][C:12]([Cl:15])=[CH:13][CH:14]=2)=[O:9])[CH2:3]1)=[O:19]

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromideHCID 866088285-chloro-thiophene-2-carboxylic acid (R)-pyrrolidin-3-ylamide hydrochloride

Product 1

HCID 587482465-chloro-thiophene-2-carboxylic acid [(R)-1-(2-bromo-acetyl)-pyrrolidin-3-yl]-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.1 A solution of 400 mg 5-chloro-thiophene-2-carboxylic acid (R)-pyrrolidin-3-ylamide hydrochloride (example 6.2) in 5 ml THF was treated with 0.31 ml TEA and 0.16 ml bromo acetylbromide. The reaction mixture was stirred over night. The precipitate was filtered and washed with THF. The filtrate was concentrated. The crude product was purified by chromatography (silica gel; gradient: CH2Cl2 to CH2Cl2/MeOH 98:2) to give 250 mg 5-chloro-thiophene-2-carboxylic acid [(R)-1-(2-bromo-acetyl)-pyrrolidin-3-yl]-amide. Off-white amorphous solid. 353.1 ([M+H]+)

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with THF
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was purified by chromatography (silica gel; gradient: CH2Cl2 to CH2Cl2/MeOH 98:2)

Sources & evidence

ORD record
ord-771dda9a09b2434684d0d8e7c2c8223e
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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