Methanesulfonyl chloride → Ammonia

HRID 348410Notes

Reaction equation

HRID 348410 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:42]([CH2:43][CH3:44])=[C:16]3[N:17]=[C:18]([C:22]4[C:23]([O:39][CH2:40][CH3:41])=[N:24][CH:25]=[C:26]([S:28]([N:31]5[CH2:36][CH2:35][N:34]([CH2:37][CH3:38])[CH2:33][CH2:32]5)(=[O:30])=[O:29])[CH:27]=4)[NH:19][C:20](=[O:21])[C:15]3=[N:14]2)=[CH:9][CH:8]=1>N1C=CC=CC=1>[NH3:6].[CH2:40]([O:39][C:23]1[C:22]([C:18]2[NH:19][C:20](=[O:21])[C:15]3[C:16](=[C:42]([CH2:43][CH3:44])[N:13]([C:10]4[CH:11]=[CH:12][C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:8][CH:9]=4)[N:14]=3)[N:17]=2)=[CH:27][C:26]([S:28]([N:31]2[CH2:36][CH2:35][N:34]([CH2:37][CH3:38])[CH2:33][CH2:32]2)(=[O:30])=[O:29])=[CH:25][N:24]=1)[CH3:41]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 135790085HCID 135790085, compound

Product 2

HCID 222AmmoniaHCID 135790098HCID 135790098, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (15 μl, 0.19 mmol) was added to an ice-cooled solution of the title compound from example 64 (93 mg, 0.17 mmol) in pyridine (2 ml), and the reaction allowed to warm to room temperature, and stirred for 90 minutes. Tlc analysis showed starting material remaining, so additional methanesulphonyl chloride (15 μl, 0.19 mmol) was added, and the reaction stirred for a further hour. The reaction was quenched by the addition of aqueous ammonium chloride solution, and extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. The residual solid was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (90:10:1) as eluant, then repeated using dichloromethane:methanol:0.88 ammonia (95:5:1) to afford the title compound, 36 mg.

Workup

  1. stirringthe reaction stirred for a further hour
  2. customThe reaction was quenched by the addition of aqueous ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residual solid was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a4d234bb448945efae23f279c6ec2874
Source dataset
uspto-grants-2007_02
Patent number
US07176311B2

Reaction notes

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