Sodium Chloride → HCID 25110505, compound

HRID 447908Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][C:5]=1[C:13]([F:16])([F:15])[F:14])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.O[N:39]=[C:40]([C:42]1[C:43]2[CH2:44][CH2:45][CH:46]([OH:51])[C:47]=2[CH:48]=[CH:49][CH:50]=1)[NH2:41].[Na+].[Cl-]>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]2[O:10][N:41]=[C:40]([C:42]3[CH:50]=[CH:49][CH:48]=[C:47]4[C:43]=3[CH2:44][CH2:45][CH:46]4[OH:51])[N:39]=2)=[CH:6][C:5]=1[C:13]([F:16])([F:15])[F:14])[CH3:2]

Participants

Conditions

Temperature: 130 °C

Procedure

In a microwave vial, a stirring solution of 4-ethoxy-3-(trifluoromethyl)benzoic acid (200 mg, 0.85 mmol) in DMF was treated with HOBt (151 mg, 1.11 mmol) and EDCI (212 mg, 1.11 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 (213 mg, 1.11 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 white solid in 51% yield (200 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-275d03f8779c45d6a67134478989fc55
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481573B2

Reaction notes

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