1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-[3-(1H-indazol-5-yl)-1,2,4-oxadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrile

HRID 2189774Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:6]([OH:8])=O)#[N:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.O[NH:38][C:39]([C:41]1[CH:42]=[C:43]2[C:47](=[CH:48][CH:49]=1)[NH:46][N:45]=[CH:44]2)=[NH:40]>CN(C=O)C>[NH:46]1[C:47]2[C:43](=[CH:42][C:41]([C:39]3[N:38]=[C:6]([C:5]4[CH:9]=[CH:10][C:11]([O:12][CH:13]([CH3:15])[CH3:14])=[C:3]([CH:4]=4)[C:1]#[N:2])[O:8][N:40]=3)=[CH:49][CH:48]=2)[CH:44]=[N:45]1

Participants

Conditions

Temperature: 80 °C

Procedure

3-Cyano-4-[(1-methylethyl)oxy]benzoic acid (can be prepared as described in WO2005/58848) (1.52 g), EDAC (2.14 g) and HOBt (1.51 g) were dissolved in DMF (30 ml) and then stirred for 5 minutes. N-hydroxy-1H-indazole-5-carboximidamide (D2) (1.3 g) was added and the reaction was heated to 80° C. for 6 hours and left to cool overnight. The solvent was removed in vacuo and the crude was partitioned between EtOAc and aq. sodium bicarbonate. The organic layer was separated, dried and evaporated to dryness in vacuo. The resulting solid was triturated with ether and ethyl acetate, washed with methanol and ether to give the title compound (816 mg) as a pink solid. MS (ES): C19H15N5O2 requires 345; found (MH+) 346

Workup

waitleft
temperatureto cool overnight
customThe solvent was removed in vacuo
customthe crude was partitioned between EtOAc and aq. sodium bicarbonate
customThe organic layer was separated
customdried
customevaporated to dryness in vacuo
customThe resulting solid was triturated with ether and ethyl acetate
washwashed with methanol and ether

Sources & evidence

ORD record: ord-bdf82a35c1e9443aa23e76e20dc27041
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324254B2

Reaction notes

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