Methanesulfonyl chloride → HCID 135740119, compound

HRID 895819Notes

Reaction equation

HRID 895819 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:45]=[CH:44][CH:43]=[CH:42][C:8]=1[CH2:9][N:10]1[C:18]2[C:17](=[O:19])[NH:16][C:15]([C:20]3[CH:25]=[C:24]([S:26]([N:29]4[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]4)(=[O:28])=[O:27])[CH:23]=[CH:22][C:21]=3[O:36][CH2:37][CH3:38])=[N:14][C:13]=2[C:12]([CH2:39][CH2:40][CH3:41])=[N:11]1>N1C=CC=CC=1>[NH3:6].[CH2:37]([O:36][C:21]1[CH:22]=[CH:23][C:24]([S:26]([N:29]2[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]2)(=[O:28])=[O:27])=[CH:25][C:20]=1[C:15]1[NH:16][C:17](=[O:19])[C:18]2[N:10]([CH2:9][C:8]3[CH:42]=[CH:43][CH:44]=[CH:45][C:7]=3[NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[N:11]=[C:12]([CH2:39][CH2:40][CH3:41])[C:13]=2[N:14]=1)[CH3:38]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 135740136HCID 135740136, compound

Product 2

HCID 222AmmoniaHCID 135740119HCID 135740119, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (31 μl, 0.40 mmol) was added to a stirred, ice-cooled solution of the title compound of Example 52 (150 mg, 0.27 mmol) in pyridine (3 ml) and the mixture stirred at room temperature for 2 hours, then evaporated under reduced pressure. The residue was treated with water (10 ml) and the resulting suspension extracted with dichloromethane (40 ml in total). The combined extracts were dried (Na2SO4) and evaporated under reduced pressure to give an orange oil which was purified by chromatography on silica gel, using ethyl acetate:methanol:0.880 aqueous ammonia (94:5:1) as eluant, to provide the title compound (62 mg) as a white foam. Found: C, 54.03; H, 5.87; N, 14.70. C29H37N7O6S2 requires C, 54.10; H, 5.79; N, 15.23%. δ (CDCl3): 1.02 (3H, t), 1.66 (3H, t), 1.90 (2H, m), 2.28 (3H, s), 2.50 (4H, m), 2.96 (2H, t), 3.10 (7H, m), 4.39 (2H, q), 5.79 (2H, s), 7.18 (2H, m), 7.36 (1H, m), 7.60 (1H, d), 7.72 (1H, d), 7.83 (1H, d), 8.80 (1H, s), 9.68 (1H, s), 10.95 (1H, s). LRMS: m/z 644 (M+1)+.

Workup

  1. customevaporated under reduced pressure
  2. additionThe residue was treated with water (10 ml)
  3. extractionthe resulting suspension extracted with dichloromethane (40 ml in total)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customto give an orange oil which
  7. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8c116669151e445ab8a9d28c2c8d7193
Source dataset
uspto-grants-2005_07
Patent number
US06916927B2

Reaction notes

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