Dimethyl Sulfone → HCID 118671891, compound

HRID 630472Notes

Reaction equation

HRID 630472 reaction equation
CC1C=CC(S(O[C@H:12]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:27]=[C:26]4[C:22]([C:23](S(C)=O)=[CH:24][N:25]4[C:28]4[N:33]=[CH:32][C:31]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=5[F:40])=[CH:30][N:29]=4)=[CH:21][CH:20]=3)=[O:18])[CH2:13]2)(=O)=O)=CC=1.[CH3:44][S:45](C)(=[O:47])=[O:46].ClC1C=C(C=CC=1)C(OO)=O.[N-:60]=[N+]=[N-].[Na+]>>[NH2:60][C@@H:12]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:27]=[C:26]3[C:22]([C:23]([S:45]([CH3:44])(=[O:47])=[O:46])=[CH:24][N:25]3[C:28]3[N:29]=[CH:30][C:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[F:40])=[CH:32][N:33]=3)=[CH:21][CH:20]=2)=[O:18])[CH2:13]1

Participants

5

Reactant 4

HCID 6213Dimethyl Sulfone2×HCID 33557Sodium AzideHCID 70297m-Chloroperbenzoic acidHCID 118676857HCID 118676857, compound2×

Product 1

HCID 118671891HCID 118671891, compound

Procedure

The target compound was obtained in three chemical steps from 68a). In the first step, compound 68a) was oxidized to the corresponding methylsulfone with use of m-chloroperoxybenzoic acid. The methylsulfone was then reacted with sodium azide and afterwards hydrogenated in analogy to the procedures 68b) and 68c), respectively. White solid. Yield: 75 mg. HPLC-MS (method 4): Rt=2.72 min; m/z [M+H]+=479.9

Sources & evidence

ORD record
ord-4c6c126c4dd144f6b2cf56fabd885bd4
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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