Hydrochloric Acid → HCID 68809668, compound

HRID 2217846Notes

Reaction equation

HRID 2217846 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[C:7]([N:12]3[CH2:16][CH2:15][C@H:14]([NH:17][CH2:18][CH2:19][O:20][Si](C(C)(C)C)(C)C)[CH2:13]3)[CH:6]=[CH:5][C:4]=2[C:3]=1[C:28]([NH:30][CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:29].Cl>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[C:7]([N:12]3[CH2:16][CH2:15][C@H:14]([NH:17][CH2:18][CH2:19][OH:20])[CH2:13]3)[CH:6]=[CH:5][C:4]=2[C:3]=1[C:28]([NH:30][CH2:31][CH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1)=[O:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68810228HCID 68810228, compound

Product 1

HCID 68809668HCID 68809668, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 6-Chloro-N-(cyclohexylmethyl)-2-[(3S)-3-[[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]amino]-1-pyrrolidinyl]-5-quinolinecarboxamide (Example 50(a)) (0.16 g) in 1,4-dioxane (1 mL) was treated with 4M HCl in 1,4-dioxane (1 mL) and stirred at room temperature for 16 hours. The reaction mixture was concentrated to dryness. Purification (HPLC, Symmetry—0.1% aqueous trifluoroacetic acid/acetonitrile) followed by conversion of the resultant product to its hydrochloride salt by treatment with hydrochloric acid (4M in 1,4-dioxane) afforded the title product (0.05 g).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customPurification (HPLC, Symmetry—0.1% aqueous trifluoroacetic acid/acetonitrile)

Sources & evidence

ORD record
ord-7bf5baf9f5344769808e78c164a60959
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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