Tetrahydrofuran → HCID 86716049, compound

HRID 1482567Notes

Reaction equation

[F:1][C:2]([C:5]1[N:10]=[CH:9][C:8]([CH:11]([N:14]2[CH2:19][CH2:18][C:17]([F:21])([F:20])[CH2:16][CH2:15]2)[CH2:12][NH2:13])=[CH:7][N:6]=1)([F:4])[CH3:3].[Cl:22][C:23]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26].C1COCC1.CCN(C(C)C)C(C)C>>[Cl:22][C:23]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:24]=1[C:25]([NH:13][CH2:12][CH:11]([C:8]1[CH:7]=[N:6][C:5]([C:2]([F:1])([F:4])[CH3:3])=[N:10][CH:9]=1)[N:14]1[CH2:19][CH2:18][C:17]([F:20])([F:21])[CH2:16][CH2:15]1)=[O:26]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 179442,3-Dichlorobenzoyl chloride

HCID 81531Diisopropylethylamine

HCID 86716012HCID 86716012, compound

Product 1

HCID 86716049HCID 86716049, compoundYield 47.4%

Procedure

2-(2-(1,1-Difluoroethyl)pyrimidin-5-yl)-2-(4,4-difluoropiperidin-1-yl)ethanamine (34 mg, 0.044 mmol, 40% pure) and 2,3-dichlorobenzoyl chloride (65 mg, 0.31 mmol), was dissolved in anhydrous THF (4400 mg, 5 ml, 61.0 mmol), DIPEA (111 mg, 0.15 ml, 0,859 mmol) was added and stirred over night. The solution was concentrated and purified by column chromatography on silica gel (petroleum ether: EtOAc=1:0 to 0:1) followed by HPLC, to afford 2,3-dichloro-N-(2-(2-(1,1-difluoroethyl)pyrimidin-5-yl)-2-(4,4-difluoropiperidin-1-yl)ethyl)benzamide (10 mg, 47% yield).

Workup

concentrationThe solution was concentrated
custompurified by column chromatography on silica gel (petroleum ether: EtOAc=1:0 to 0:1)

Sources & evidence

ORD record: ord-1f76a74bb50f47cda99fab12924a35a3
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09415055B2

Reaction notes

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