Methanesulfonyl chloride → HCID 136358673, compound

HRID 895820Notes

Reaction equation

HRID 895820 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[C:43]([CH2:44][CH2:45][CH3:46])=[C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[C:26]([S:28]([N:31]4[CH2:36][CH2:35][N:34]([CH2:37][CH3:38])[CH2:33][CH2:32]4)(=[O:30])=[O:29])[CH:25]=[CH:24][C:23]=3[O:39][CH2:40][CH2:41][CH3:42])[NH:19][C:20](=[O:21])[C:15]2=[N:14]1>N1C=CC=CC=1>[CH2:37]([N:34]1[CH2:35][CH2:36][N:31]([S:28]([C:26]2[CH:25]=[CH:24][C:23]([O:39][CH2:40][CH2:41][CH3:42])=[C:22]([C:18]3[NH:19][C:20](=[O:21])[C:15]4[C:16](=[C:43]([CH2:44][CH2:45][CH3:46])[N:13]([C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=5[NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[N:14]=4)[N:17]=3)[CH:27]=2)(=[O:30])=[O:29])[CH2:32][CH2:33]1)[CH3:38]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 136481316HCID 136481316, compound

Product 1

HCID 136358673HCID 136358673, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

Methanesulphonyl chloride (0.156 ml, 2.0 mmol) was added to a stirred solution of the title compound of Example 116 (583 mg, 1.0 mmol) in pyridine (8 ml), under nitrogen, and the resulting solution stirred at 50° C. for 18 hours, then evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water, then the separated organic phase washed with brine, dried (MgSO4) and evaporated under reduced pressure. The resulting brown foam was purified by column chromatography on silica gel, using an elution gradient of dichloromethane:methanol (100:0 to 99:1 to 98:2 to 97:3), to yield the title compound (32%) as a cream foam. Found: C, 53.96; H, 6.01; N, 14.38. C30H39N7O6S2; 0.60 H2O requires C, 53.89; H, 6.06; N, 14.67%. δ (CDCl3): 0.91 (3H, t), 1.01 (3H, t), 1.19 (3H, t), 1.75 (2H, m), 2.07 (2H, m), 2.40 (2H, q), 2.53 (4H, m), 2.93 (2H, t), 3.07 (3H, s), 3.09 (4H, m), 4.29 (2H, t), 7.16 (2H, m), 7.35 (2H, m), 7.57 (1H, t), 7.82 (2H, d), 8.80 (1H, s), 10.74 (1H, s). LRMS: m/z 658 (M+1)+.

Workup

  1. customevaporated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. washthe separated organic phase washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe resulting brown foam was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ed799ec36be342c4b5150a760d113ea0
Source dataset
uspto-grants-2005_07
Patent number
US06916927B2

Reaction notes

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