Water → HCID 67266313, compound

HRID 1971310Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C@H:10]1[CH2:15][C@H:14]([NH:16][C:17]([C:19]2[CH:28]=[CH:27][C:22]3[O:23][CH2:24][CH2:25][O:26][C:21]=3[CH:20]=2)=[O:18])[CH2:13][CH2:12][N:11]1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].Br[CH2:37][CH2:38][O:39][CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][O:41]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[O:23]1[CH2:24][CH2:25][O:26][C:21]2[CH:20]=[C:19]([C:17]([NH:16][C@@H:14]3[CH2:13][CH2:12][N:11]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@@H:10]([C:2]4[N:3]([CH2:37][CH2:38][O:39][CH:40]5[CH2:45][CH2:44][CH2:43][CH2:42][O:41]5)[C:4]5[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=5[N:1]=4)[CH2:15]3)=[O:18])[CH:28]=[CH:27][C:22]1=2

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (2R,4R)-tert-butyl 2-(1H-benzo[d]imidazol-2-yl)-4-(2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamido)piperidine-1-carboxylate (200 mg, 0.418 mmol) in DMF (2 mL) was added 2-(2-bromoethoxy)-tetrahydro-2H-pyran (114 mg, 0.543 mmol) and K2CO3 (116 mg, 0.836 mmol), and the reaction mixture was stirred at 80° C. for over night. Water and ethyl acetate were added to the mixture, organic layer was separated and dried over MgSO4 and concentrated. The residue was purified by HPLC with 0.1% HCOOH in water/0.1% HCOOH in ACN from 45-70% to give the named compound as white solid 90 mg (35%). LC-MS: 607.2 (t=2.9 min).

Workup

customwas separated
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by HPLC with 0.1% HCOOH in water/0.1% HCOOH in ACN from 45-70%

Sources & evidence

ORD record: ord-9fbbf636a4b64ae98303d36430c3c258
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431597B2

Reaction notes

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