(Methylsulfonyl)-carbamic acid ethyl ester → N-[6-Chloro-2-[(3S)-3-[[[(methylsulfonyl)amino]carbonyl]amino]-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide

HRID 2217893Notes

Reaction equation

HRID 2217893 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([Cl:27])[C:13]=3[NH:17][C:18](=[O:26])[CH2:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[N:8]=2)[CH2:3]1.C([O:30][C:31](=O)[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])C>>[Cl:27][C:12]1[C:13]([NH:17][C:18](=[O:26])[CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:4]1[CH2:5][CH2:6][C@H:2]([NH:1][C:31]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[O:30])[CH2:3]1)[CH:16]=[CH:15]2

Participants

3

Reactant 2

HCID 1201508(Methylsulfonyl)-carbamic acid ethyl esterHCID 59768628N-[2-[(3S)-3-Amino-1-pyrrolidinyl]-6-chloro-5-quinolinyl]-cyclohexaneacetamide

Product 1

HCID 59768640N-[6-Chloro-2-[(3S)-3-[[[(methylsulfonyl)amino]carbonyl]amino]-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamideYield 8.1%

Procedure

N-[2-[(3S)-3-Amino-1-pyrrolidinyl]-6-chloro-5-quinolinyl]-cyclohexaneacetamide (Example 31) (0.15 g) and (methylsulfonyl)-carbamic acid ethyl ester (0.065 g) were heated with a single mode microwave in a sealed 10 mL vial for 30 minutes at 130° C. The residue was purified on a Varian® NH2 cartridge washed with methanol (50 mL) and eluted with acetic acid:methanol (10:90) to afford the title product (0.016 g).

Workup

  1. customThe residue was purified on a Varian® NH2 cartridge
  2. washwashed with methanol (50 mL)
  3. washeluted with acetic acid:methanol (10:90)

Sources & evidence

ORD record
ord-f396b0db1e3a490b99b7d01917cf3561
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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