Water → HCID 178505020, compound

HRID 1035822Notes

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]1

Participants

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-5486a5a32b2a4cbaa751ac313b3fd253
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546400B2

Reaction notes

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