Hydrochloric Acid → HCID 59753591, compound

HRID 1693463Notes

Reaction equation

HRID 1693463 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:37])[C@@H:15]([NH:24][C:25]([C:27]2[NH:36][C:30]3=[CH:31][N:32]=[C:33]([Cl:35])[CH:34]=[C:29]3[CH:28]=2)=[O:26])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)(C)(C)C.Cl.O1CCOCC1>CO>[NH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:37])[C@@H:15]([NH:24][C:25]([C:27]2[NH:36][C:30]3=[CH:31][N:32]=[C:33]([Cl:35])[CH:34]=[C:29]3[CH:28]=2)=[O:26])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59753532HCID 59753532, compound

Product 1

HCID 59753591HCID 59753591, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of {1-[2-(S)-[(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)propionyl]piperidin-4-yl}carbamic acid tert-butyl ester (EXAMPLE 230, 500 mg, 0.92 mmol) in methanol (12 mL) was added a solution of 4M HCl in dioxane (0.69 mL, 2.76 mmol) and the reaction stirred for 48 h. The resulting precipitate was filtered and washed with ethyl acetate to give the title compound as the hydrochloride salt as a pale yellow powder. m/z (ES+)=444.16 [M+H]+; RT=2.65 min. The product was dissolved in saturated sodium bicarbonate solution. Solvent was removed in vacuo and the crude material dissolved in THF (30 mL). The solution was filtered through celite and solvent removed in vacuo to give the title compound as a yellow powder. m/z (ES+)=444.32 [M+H]+; RT=2.59 min.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-11a79d9188824c96bd60a623eb6f5970
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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