HCID 86587886, compound → HCID 86587885, compound

HRID 1244012Notes

Reaction equation

HRID 1244012 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][NH:10][C:11]([N:13]1[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][CH2:20][C:21]2[CH:30]=[C:29]3[C:24]([CH2:25][CH2:26][C:27](=[O:32])[N:28]3[CH3:31])=[CH:23][C:22]=2[O:33][CH3:34])[C@@H:14]1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[S:12])(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[NH2:7][CH2:8][CH2:9][NH:10][C:11]([N:13]1[CH2:18][CH2:17][CH2:16][CH:15]([NH:19][CH2:20][C:21]2[CH:30]=[C:29]3[C:24]([CH2:25][CH2:26][C:27](=[O:32])[N:28]3[CH3:31])=[CH:23][C:22]=2[O:33][CH3:34])[CH:14]1[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[S:12]

Participants

4

Reactant 1

HCID 86587886HCID 86587886, compound

Product 1

HCID 86587885HCID 86587885, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

[2-({3-[(6-Methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-ylmethyl)-amino]-(2S,3S)-2-phenyl-piperidine-1-carbothioyl}-amino)-ethyl]-carbamic acid tert-butyl ester (800 mg, 1.38 mmol) was stirred in a mixture of 30 mL methylene chloride and 10 mL trifluoroacetic acid at room temperature for 4 hours. The solvent was removed and the residue was partitioned between ethyl acetate and satd. K2CO3. The organics were separated, dried over MgSO4, filtered, and concentrated to give 3-[(6-Methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-ylmethyl)-amino]-2-phenyl-piperidine-1-carbothioic acid (2-amino-ethyl)-amide. Rf=0.18 (90:10:1 methylene chloride/methanol/satd. aq. NH4OH).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between ethyl acetate and satd
  3. customThe organics were separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d56cd05e6ee14199abcfb4063d8b70c9
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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