Methanesulfonamide → HCID 22117182, compound

HRID 1275922Notes

Reaction equation

HRID 1275922 reaction equation
[CH3:1][C:2]1[CH:34]=[CH:33][C:5]2[CH:6]([C:16]3[C:17](=[S:32])[NH:18][C:19](=[O:31])[N:20]([CH2:22][C:23]4[O:24][CH:25]=[C:26]([C:28](O)=[O:29])[N:27]=4)[CH:21]=3)[C:7]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:8]=3[CH:9]=[CH:10][C:4]=2[CH:3]=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.[CH3:59][S:60]([NH2:63])(=[O:62])=[O:61].C(N(CC)C(C)C)(C)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH3:15][C:12]1[CH:13]=[CH:14][C:7]2[CH:6]([C:16]3[C:17](=[S:32])[NH:18][C:19](=[O:31])[N:20]([CH2:22][C:23]4[O:24][CH:25]=[C:26]([C:28]([NH:63][S:60]([CH3:59])(=[O:62])=[O:61])=[O:29])[N:27]=4)[CH:21]=3)[C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:34][C:33]=3[CH:10]=[CH:9][C:8]=2[CH:11]=1

Participants

7

Reactant 4

HCID 72879MethanesulfonamideHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 22117262HCID 22117262, compound

Product 1

HCID 22117182HCID 22117182, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

The product of example 37(0.2 g), bromo-tris(pyrrolidino)-phosphonium hexafluorophosphate (0.38 g), 4-dimethylaminopyridine (0.07 g), methanesulphonamide (0.095 g) and N,N-diisopropylethylamine (0.43 ml) in N,N-dimethylformamide (2 ml) was stirred at room temperature for 16 h. The mixture was partitioned between aqueous tartaric acid and ethyl acetate. The organic solution was dried (MgSO4) and evaporated. Purification was by reverse phase silica gel chromatography (C18-sep-pak) eluting with 50% methanol in 0.1% aqueous ammonium acetate. Yield 0.032 g.

Workup

  1. customThe mixture was partitioned between aqueous tartaric acid and ethyl acetate
  2. dry with materialThe organic solution was dried (MgSO4)
  3. customevaporated
  4. customPurification
  5. washeluting with 50% methanol in 0.1% aqueous ammonium acetate

Sources & evidence

ORD record
ord-234ce32e4e324122876ab9a89f798431
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Reaction notes

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