Hydrochloric Acid → HCID 67013086, compound

HRID 2250441Notes

Reaction equation

HRID 2250441 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[CH:33]=[C:32]([C:34]4[S:35][C:36]([Cl:39])=[CH:37][CH:38]=4)[O:31][N: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[CH:33]=[C:32]([C:34]4[S:35][C:36]([Cl:39])=[CH:37][CH:38]=4)[O:31][N: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 86595864HCID 86595864, compound

Product 1

HCID 67013086HCID 67013086, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 600 mg (1.01 mmol) of 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-(2-methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide hydrochloride (example 10 (vi)) in 50 mL CH2Cl2 2 mL (2.02 mmol) of a 1M solution of BBr3 in CH2Cl2 were added. The mixture was stirred at room temperature for 6 h. After standing over night the solvent was removed in vacuo and the residue was purified by preparative HPLC (eluent: CH3CN/H2O/0.1% CF3COOH). The fractions containing the product were combined and concentrated in vacuo. The residue was dissolved in CH2Cl2 an washed with 0.1N NaOH solution. The solvent was removed in vacuo and the residue lyophilized with 2.5 equivalents of 1N HCl yielding 464 mg (79%) of the hydrochloride salt of the desired product.

Workup

  1. waitAfter standing over night
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified by preparative HPLC (eluent: CH3CN/H2O/0.1% CF3COOH)
  4. additionThe fractions containing the product
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in CH2Cl2
  7. washan washed with 0.1N NaOH solution
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3c8a53c453134df69b50285463a9f2df
Source dataset
uspto-grants-2008_01
Patent number
US07317027B2

Reaction notes

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