Hydrochloric Acid → HCID 178527292, compound

HRID 1429389Notes

Reaction equation

HRID 1429389 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[S:17]([N:20]2[CH2:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[CH2:24][O:23][CH2:22][C@H:21]2[CH2:32][C:33]#[N:34])(=[O:19])=[O:18])[CH:10]=[CH:9][CH:8]=1.Cl>CN(C=O)C>[NH:1]1[C:33]([CH2:32][C@H:21]2[N:20]([S:17]([C:15]3[CH:14]=[CH:13][CH:12]=[C:11]4[C:16]=3[N:7]=[CH:8][CH:9]=[CH:10]4)(=[O:19])=[O:18])[CH2:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[CH2:24][O:23][CH2:22]2)=[N:34][N:3]=[N:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 71269471HCID 71269471, compound

Product 1

HCID 178527292HCID 178527292, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

To the mixture of sodium azide (48 mg, 0.75 mmol) and ammonium chloride (40 mg, 0.75 mmol) in dry DMF (5 mL) was added compound 24 (100 mg, 0.25 mmol) under a nitrogen atmosphere. The mixture was stirred at 125° C. for 48 hr. The cooled reaction was poured into ice water and acidified to pH=1 with 1N HCl. The mixture was concentrated in vacuo and purified by Prep-HPLC to obtain compound 25 (30 mg, 27% yield). LCMS (m/z): 437.2 (MH+).

Workup

  1. customThe cooled reaction
  2. concentrationThe mixture was concentrated in vacuo
  3. custompurified by Prep-HPLC

Sources & evidence

ORD record
ord-e26c1324667f4d2f8b1706b3072eb1f5
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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