Hydrochloric Acid → HCID 67012312, compound

HRID 2250448Notes

Reaction equation

HRID 2250448 reaction equation
Cl.[CH:2]([N:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12]([C:14]2[N:27]([CH2:28][C:29]3[S:33][C:32]4[CH:34]=[C:35]([Cl:38])[CH:36]=[CH:37][C:31]=4[CH:30]=3)[C:17]3=[CH:18][N:19]=[C:20]([O:22][CH2:23][CH2:24][O:25]C)[CH:21]=[C:16]3[CH:15]=2)=[O:13])[CH2:7][CH2:6]1)([CH3:4])[CH3:3].B(Br)(Br)Br.Cl>C(Cl)Cl>[CH:2]([N:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12]([C:14]2[N:27]([CH2:28][C:29]3[S:33][C:32]4[CH:34]=[C:35]([Cl:38])[CH:36]=[CH:37][C:31]=4[CH:30]=3)[C:17]3=[CH:18][N:19]=[C:20]([O:22][CH2:23][CH2:24][OH:25])[CH:21]=[C:16]3[CH:15]=2)=[O:13])[CH2:7][CH2:6]1)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 86595867HCID 86595867, compound

Product 1

HCID 67012312HCID 67012312, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 810 mg (1.236 mmol) of 1-(6-Chloro-benzo[b]thiophen-2-ylmethyl)-5-(2-methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide hydrochloride in 80 mL CH2Cl2 2.472 mL of a 1M solution of BBr3 in CH2Cl2 were added. The mixture was stirred at room temperature for 30 min. The solvent was removed in vacuo and lyophilized. The residue was purified by preparative HPLC (eluent: CH3CN/H2O/0.1% CF3COOH). The fractions containing the product were combined, concentrated in vacuo and lyophilized with 2.5 equivalents of 1N HCl yielding the hydrochloride salt of the desired product.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was purified by preparative HPLC (eluent: CH3CN/H2O/0.1% CF3COOH)
  3. additionThe fractions containing the product
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5489116f45fe406685de97720432093e
Source dataset
uspto-grants-2008_01
Patent number
US07317027B2

Reaction notes

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