HCID 25171033, compound → HCID 68745687, compound

HRID 2093593Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:38]([CH3:40])[CH3:39])[C:6]2[O:10][C:9]([C:11]3[CH:36]=[CH:35][C:14]([C:15]([NH:17][CH2:18][CH:19]4[CH2:24][CH2:23][N:22](C(OCC5C=CC=CC=5)=O)[CH2:21][CH2:20]4)=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:37]=1)#[N:2]>CO.O1CCCC1.[Pd]>[C:1]([C:3]1[CH:4]=[C:5]([CH:38]([CH3:40])[CH3:39])[C:6]2[O:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([NH:17][CH2:18][CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[O:16])=[CH:35][CH:36]=3)=[N:8][C:7]=2[CH:37]=1)#[N:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of benzyl 4-({[4-(5-cyano-7-isopropyl-1,3-benzoxazol-2yl)benzoyl]amino}methyl)piperidine-1-carboxylate (2.19 g, EXAMPLE 35) in methanol (30 ml) and tetrahydrofuran (7 ml) was added 10% palladium on carbon (500 mg, 4.70 mmol). The mixture was flushed with nitrogen, then flushed with hydrogen, and then warmed to 50° C. and stirred for 3 h under a hydrogen balloon at this temperature, at which point LC/MS analysis showed no starting material. The mixture was filtered through a plug of Celite, washing liberally with methanol, and then concentrated to provide the title compound (1.7 g, 103%). Mass spectrum (ESI) 403.6 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.32 (d, J=8 Hz, 2H), 7.94 (d, J=8.5 Hz, 2H), 7.93 (s, 1H), 7.51 (s, 1H), 6.33 (br s, 1H), 3.44-3.54 (m, 2H), 3.40 (m, 2H), 3.13 (br d, 2H), 2.63 (br t, 2H), 1.77 (m, 2H), 1.46 (d, J=6.5 Hz, 6H), 1.26 (m, 2H).

Workup

customThe mixture was flushed with nitrogen
customflushed with hydrogen
filtrationThe mixture was filtered through a plug of Celite
washwashing liberally with methanol
concentrationconcentrated

Sources & evidence

ORD record: ord-2798b46a54ca41f3afcedff285ba5744
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445480B2

Reaction notes

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