Water → HCID 178505020, compound
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([NH:14][C:15]3[CH:16]=[C:17]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH:18]=[CH:19][CH:20]=3)=[N:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].[N-:26]=[N+:27]=[N-:28].[Na+].[Cl-].[NH4+].O>CN(C=O)C>[NH:26]1[C:1]([C:3]2[CH:8]=[CH:7][C:6]([C:9]3[O:13][C:12]([NH:14][C:15]4[CH:16]=[C:17]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH:18]=[CH:19][CH:20]=4)=[N:11][CH:10]=3)=[CH:5][CH:4]=2)=[N:2][N:28]=[N:27]1Participants
Conditions
- Temperature
- 120 °C
Procedure
N-(3-((5-(4-cyanophenyl)oxazol-2-yl)amino)phenyl)methanesulfonamide 7 (0.12 g, 0.338 mmol) was dissolved in anhydrous DMF (10 mL), Sodium azide (0.088 g, 1.35 mmol) and ammonium chloride (0.072 g, 1.35 mmol) were added to above solution. Resulting suspension was heated at 120° C. for overnight (14 hours). Reaction was cooled down and water was added. Resulting (precipitated) solid was filtered, washed with water, methanol, and water. This was further purified by dissolving into DMSO and re-precipitated with addition of water. Resulting solid was filtered, washed with water, methanol and dried under high vacuum to yield N-(3-((5-(4-(1H-tetrazol-5-yl)phenyl)oxazol-2-yl)amino)phenyl)methanesulfonamide 41 (0.12 g, 90%) as a white solid. MS (ES) m/z 398 (M+H+).
Workup
- customResulting suspension
- customReaction
- temperaturewas cooled down
- customResulting
- custom(precipitated) solid
- filtrationwas filtered
- washwashed with water, methanol, and water
- customThis was further purified
- dissolutionby dissolving into DMSO
- customre-precipitated with addition of water
- customResulting solid
- filtrationwas filtered
- washwashed with water, methanol
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-0fc2a3f1d318485f998b615e5ab1bfcd
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865709B2
Reaction notes
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