Benzoyl chloride → (S)-N-(1-{4-[1-(5-Phenyl-[1,2,4]oxadiazol-3-yl)-piperidin-4-yl]-phenyl}-ethyl)acetamide

HRID 1470766Notes

Reaction equation

[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[NH:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:25]=[CH:24][C:23]([C@@H:26]([NH:28][C:29](=[O:31])[CH3:30])[CH3:27])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)=[NH:13].C(N(CC)CC)C>C1COCC1>[C:2]1([C:1]2[O:8][N:13]=[C:12]([N:14]3[CH2:19][CH2:18][CH:17]([C:20]4[CH:21]=[CH:22][C:23]([C@@H:26]([NH:28][C:29](=[O:31])[CH3:30])[CH3:27])=[CH:24][CH:25]=4)[CH2:16][CH2:15]3)[N:11]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

0.019 mL (0.16 mmol) Benzoyl chloride are added to a mixture of 45.7 mg (0.15 mmol) (S)—N-(1-{4-[1-(N-hydroxycarbamimidoyl)-piperidin-4-yl]-phenyl}-ethyl)-acetamide (XXVII.2) and 0.063 mL (0.45 mmol) triethylamine in 4 mL THF. The mixture is stirred for 12 h at 80° C. and is subsequently purified by HPLC (RP C18 Sunfire; water (+0.1% TFA)/MeOH) to yield the desired product.

Workup

customis subsequently purified by HPLC (RP C18 Sunfire; water (+0.1% TFA)/MeOH)

Sources & evidence

ORD record: ord-ffc0523908164dceb04a66236f0c7647
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006450B2

Reaction notes

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