Sodium Chloride → 2-ethoxy-5-(3-(1-hydroxy-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)benzonitrile

HRID 1048934Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[C:6]([OH:8])=O)#[N:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.O[N:37]=[C:38]([C:40]1[C:41]2[CH2:42][CH2:43][CH:44]([OH:49])[C:45]=2[CH:46]=[CH:47][CH:48]=1)[NH2:39].[Na+].[Cl-]>CN(C=O)C>[CH2:13]([O:12][C:11]1[CH:10]=[CH:9][C:5]([C:6]2[O:8][N:39]=[C:38]([C:40]3[CH:48]=[CH:47][CH:46]=[C:45]4[C:41]=3[CH2:42][CH2:43][CH:44]4[OH:49])[N:37]=2)=[CH:4][C:3]=1[C:1]#[N:2])[CH3:14]

Participants

Conditions

Temperature: 130 °C

Procedure

In a microwave vial, a stirring solution of 3-cyano-4-ethoxybenzoic acid (200 mg, 1.05 mmol) in DMF was treated with HOBt (185 mg, 1.36 mmol) and EDCI (260 mg, 1.36 mmol) at room temperature. The reaction was stirred for 20 min followed by addition, in a single portion, of N′,1-dihydroxy-2,3-dihydro-1H-indene-4-carboximidamide (261 mg, 1.36 mmol). The reaction was stirred for additional 30 min at room temperature and then heated to 130° C. for 35 min in the initiator. The reaction was diluted using a saturated solution of NaCl and extracted with EtOAc (80 ml×3). The organic phase was dried over Na2SO4 anhydrous and concentrated under reduced pressure. The product was purified by column chromatography using CH2Cl2:MeOH (9:1) to offer the product as pale yellow solid in 79% yield (274 mg).

Workup

stirringThe reaction was stirred for additional 30 min at room temperature
additionThe reaction was diluted
extractionextracted with EtOAc (80 ml×3)
dry with materialThe organic phase was dried over Na2SO4 anhydrous
concentrationconcentrated under reduced pressure
customThe product was purified by column chromatography

Sources & evidence

ORD record: ord-27e358e5c67a4c51b20a6729d4c077c9
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382217B2

Reaction notes

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