Dichloromethane → HCID 86716244, compound

HRID 512211Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(NC)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:16][C:17]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20].CC[N:29]([CH:33](C)C)C(C)C.C(Cl)[Cl:37]>>[Cl:37][C:17]1([CH3:16])[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][CH:18]1[C:19]([NH:29][CH2:33][C:8]1([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)=[O:20]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 81531Diisopropylethylamine

HCID 28008992,3-Dimethylbenzoyl chloride

HCID 83692057HCID 83692057, compound

Product 1

HCID 86716244HCID 86716244, compoundYield 66%

Procedure

A mixture of [4-(4-chloro-phenyl)-tetrahydro-pyran-4-yl]-methylamine (67.7 mg, 0.3 mmol), 2,3-dimethylbenzoyl chloride (53 mg, 0.315 mmol) and DIPEA (78 mg, 0.60 mmol) in DCM (1.5 mL) was stirred at room temperature for 16 h. The mixture was purified by preparative HPLC to yield the title compound (70.5 mg, yield: 66%). 1H NMR (CDCl3 300 MHz): δ ppm 7.40-6.98 (m, 7H), 5.35 (bs, 1H), 3.95-3.87 (m, 2H), 3.70 (d, 2H), 3.70-3.60 (m, 2H), 2.31 (s, 3H), 2.23 (s, 3H), 2.18-1.92 (m, 4H). LCMS (MH+): m/z=358.0, tR (minutes, Method B)=1.03

Workup

customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record: ord-8bd27391400940f084bbe4be04bcb8cf
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102591B2

Reaction notes

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