Dicyclohexylcarbodiimide → HCID 59556614, compound

HRID 1172983Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])/[C:5](=[N:7]/[OH:8])/[NH2:6].[NH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=O)=[C:19]([Cl:26])[CH:18]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CC(=O)OCC.C(#N)C>[Cl:26][C:19]1[CH:18]=[C:17]([CH:25]=[CH:24][C:20]=1[C:21]1[O:8][N:7]=[C:5]([C:4]2[CH:9]=[CH:10][C:11]([O:12][CH:13]([CH3:15])[CH3:14])=[C:2]([Cl:1])[CH:3]=2)[N:6]=1)[NH2:16]

Participants

Conditions

Temperature: 120 °C

Procedure

(Z)-3-chloro-N′-hydroxy-4-isopropoxybenzimidamide (0.5 g, 2.187 mmol), 4-amino-2-chlorobenzoic acid (0.413 g, 2.405 mmol), DCC (0.496 g, 2.405 mmol), HOBT (0.368 g, 2.405 mmol) were placed in an 80 ml microwave vial and Acetonitrile (12.01 ml) was added. The reaction mixture was stirred for 5 minutes at room temperature before the addition of DIEA (0.840 ml, 4.81 mmol). The reaction mixture was heated to 120° C. for 30 min in a microwave. TLC (50% EA/Hept) indicated 4 spots Rf 0.8, 0.6, 0.5 and 0.3. LCMS (2007—9349) indicated by UV 16% (2.61 mins) to (M+H) 364.31. The solvent was removed and the crude material purified by FCC (50% EA/Hept) to afford 3-chloro-4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)aniline (534 mg, 1.466 mmol, 67.1% yield). LCMS (Table A, Method b) indicated a 99% by UV (3.10 mins) and 92% by ELSD (3.06 mins) to (M+H)+ 364.12.

Workup

customindicated by UV 16% (2.61 mins) to (M+H) 364.31
customThe solvent was removed
customthe crude material purified by FCC (50% EA/Hept)

Sources & evidence

ORD record: ord-e00fac55887d4fd6a9d4fd7f76aab247
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834039B2

Reaction notes

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