Hydrochloric Acid → HCID 11166326, compound

HRID 2217861Notes

Reaction equation

HRID 2217861 reaction equation
[Cl:1][C:2]1[C:3]([NH:28][C:29](=[O:37])[CH2:30][CH2:31][CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:16][CH2:15][C@H:14]([NH:17][CH2:18][CH2:19][O:20][Si](C(C)(C)C)(C)C)[CH2:13]1)[CH:6]=[CH:5]2.Cl>ClCCl.CO>[Cl:1][C:2]1[C:3]([NH:28][C:29](=[O:37])[CH2:30][CH2:31][CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:16][CH2:15][C@H:14]([NH:17][CH2:18][CH2:19][OH:20])[CH2:13]1)[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68808733HCID 68808733, compound

Product 1

HCID 11166326HCID 11166326, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a stirred solution of N-[6-chloro-2-[(3S)-3-[[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]amino]-1-pyrrolidinyl]-5-quinolinyl]-cyclopentanepropanamide (Example 63(a)) (200 mg) in dichloromethane:methanol 1:1 (3 mL) under nitrogen, was added HCl (1 mL, 4M solution in dioxane). The reaction mixture was stirred at room temperature for 30 minutes, then evaporated to dryness. Purification (HPLC, Symmetry—0.1% aqueous trifluoroacetic acid/acetonitrile) gave the title compound as a solid (35 mg).

Workup

  1. customevaporated to dryness
  2. customPurification (HPLC, Symmetry—0.1% aqueous trifluoroacetic acid/acetonitrile)

Sources & evidence

ORD record
ord-b7565b7d36cd4e20b7c734459726e0d2
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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