4-Aminobenzoic Acid → HCID 59556548, compound

HRID 1172985Notes

Reaction equation

HRID 1172985 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)=[CH:19][CH:18]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.CCN(C(C)C)C(C)C>>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]=[C:21]([C:20]3[CH:24]=[CH:25][C:17]([NH2:16])=[CH:18][CH:19]=3)[O:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 5

HCID 9784-Aminobenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 595565653-chloro-N'-hydroxy-4-propan-2-yloxybenzenecarboximidamide

Product 1

HCID 59556548HCID 59556548, compoundYield 50.6%

Conditions

Temperature
150 °C

Procedure

(Z)-3-chloro-N′-hydroxy-4-isopropoxybenzimidamide (1 g, 4.37 mmol), 4-aminobenzoic acid (0.660 g, 4.81 mmol), HOBT (0.737 g, 4.81 mmol), DCC (0.992 g, 4.81 mmol) and DIEA (1.680 ml, 9.62 mmol) were combined in a microwave vial. The reaction mixture was heated in the microwave for 20 minutes at 150° C. The reaction mixture was filtered to remove the urea formed in the reaction and the solvent was removed in vacuo. The crude material was purified by FCC (50% ethyl acetate/heptane) to afford 4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)aniline (729 mg, 2.211 mmol, 50.6% yield) as an off white solid: LCMS (Table A, Method b) 3.00 min, (M+H)+ 330.13.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the urea
  3. customformed in the reaction
  4. customthe solvent was removed in vacuo
  5. customThe crude material was purified by FCC (50% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-24291492e14549d5ab659910f4c1a04e
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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