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Pyridine → HCID 69700784, compound

HRID 382340
Notes
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Reaction equation

HRID 382340 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[NH:10][C@H:11]1[C:20]2[C:15](=[CH:16][C:17]3[CH2:23][CH2:22][CH2:21][C:18]=3[CH:19]=2)[NH:14][C@@H:13]([CH3:24])[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:33]([O:35][CH2:36][CH3:37])=[O:34]>ClCCl>[CH2:36]([O:35][C:33]([N:14]1[C:15]2[C:20](=[CH:19][C:18]3[CH2:21][CH2:22][CH2:23][C:17]=3[CH:16]=2)[C@H:11]([NH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:25])[CH2:12][C@@H:13]1[CH3:24])=[O:34])[CH3:37]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 69700254HCID 69700254, compound

Product 1

HCID 69700784HCID 69700784, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of cis-(2-methyl-2,3,4,6,7,8-hexahydro-1H-cyclopenta[g]quinolin-4-yl)-carbamic acid benzyl ester (Example 1A) (2.0 g, 5.9 mmol) in anhydrous dichloromethane (50 mL) was added pyridine (1.0 mL). The mixture was cooled to 0° C., and ethyl chloroformate (1.0 mL) was slowly added. The reaction was stirred at 0° C. for 30 min, then at room temperature for 4 h. The reaction mixture was washed twice with 25 mL of 2N HCl. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel chromatography using 15% ethyl acetate/hexanes as eluent afforded the title compound (500 mg). 1H NMR (CDCl3) δ1.1 (d, 3H), 1.2 (t, 3H), 4.2 (m, 2H), 5.2 (s, 2H), 7.0 (s, 1H), 7.3 (s, 1H), 7.4 (m, 5H).

Workup

  1. waitat room temperature for 4 h
  2. washThe reaction mixture was washed twice with 25 mL of 2N HCl
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-8ce05fbabf814f3b83d2cdbc3f4e7cd8
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06310075B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes