Dichloromethane → HCID 71224725, compound

HRID 710016Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15](=[O:43])[C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[CH3:34])[CH2:24][CH2:23]3)=[C:18]([NH:35][C:36]([C:38]3[O:39][CH:40]=[CH:41][CH:42]=3)=[O:37])[CH:17]=2)[CH2:9]1)=O)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O.[CH2:54]([N:56]=[C:57]=[O:58])[CH3:55]>CO.N1C=CC=CC=1>[CH2:54]([NH:56][C:57]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15](=[O:43])[C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:23][CH2:24][N:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[CH3:34])[CH2:26][CH2:27]3)=[C:18]([NH:35][C:36]([C:38]3[O:39][CH:40]=[CH:41][CH:42]=3)=[O:37])[CH:17]=2)[CH2:9]1)=[O:58])[CH3:55]

Participants

Conditions

Temperature: 45 °C

Procedure

(R)-3-[3-[(Furan-2-carbonyl)-amino]-4-(4-o-tolyl-piperazin-1-yl)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester (0.12 g, 0.204 mmol) was stirred with a mixture of DCM (1.0 mL) and TFA (1.0 mL) for 4 h. LC-MS indicated the completion of deprotection. The mixture was concentrated and dissolved in pyridine (5.0 mL). EtNCO (29 mg, 0.41 mmol) was added and the reaction mixture was stirred at 45° C. for 6 h. Pyridine was rotavaped out and the crude was dissolved in methanol and purified on preparatory HPLC using water/methanol as eluent to give desired product (0.02 g, 18%).

Workup

concentrationThe mixture was concentrated
dissolutiondissolved in pyridine (5.0 mL)
custompurified on preparatory HPLC

Sources & evidence

ORD record: ord-011b4e1672e04789a4b74c640b425dae
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181226B2

Reaction notes

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