Carbonic acid, bis(1,1-dimethylethyl) ester → [1-[6-Chloro-5-[(cyclohexylacetyl)amino]-2-quinolinyl]-3-pyrrolidinyl](2-hydroxyethyl)-carbamic acid 1,1-dimethylethyl ester

HRID 2217852Notes

Reaction equation

HRID 2217852 reaction equation
[Cl:1][C:2]1[C:3]([NH:21][C:22](=[O:30])[CH2:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]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.[C:31]([O:35][C:36](=O)[O:37]C(C)(C)C)([CH3:34])([CH3:33])[CH3:32]>ClCCl.CO>[CH3:32][C:31]([O:35][C:36](=[O:37])[N:17]([CH:14]1[CH2:15][CH2:16][N:12]([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[C:3]=3[NH:21][C:22](=[O:30])[CH2:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[N:8]=2)[CH2:13]1)[CH2:18][CH2:19][OH:20])([CH3:34])[CH3:33]

Participants

5

Reactant 2

HCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 59768616HCID 59768616, compound

Product 1

HCID 11341570[1-[6-Chloro-5-[(cyclohexylacetyl)amino]-2-quinolinyl]-3-pyrrolidinyl](2-hydroxyethyl)-carbamic acid 1,1-dimethylethyl esterYield 32.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-[6-chloro-2-[(3S)-3-[(2-hydroxyethyl)amino]-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide (Example 36) (1 g) in dichloromethane (5 mL) and methanol (2 mL) was added di-tert-butyl-carbonate (1 g). The mixture was stirred at room temperature for 18 hours and absorbed onto silica. Purification (SiO2, methanol:dichloromethane 5:95 as eluant) gave the title compound as a solid (400 mg).

Workup

  1. customabsorbed onto silica
  2. customPurification (SiO2, methanol:dichloromethane 5:95 as eluant)

Sources & evidence

ORD record
ord-82e8889d493c4fb9b810829fb9054a20
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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