Triethylamine → HCID 59737342, compound

HRID 1907701Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C.[Cl:28][CH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1>C(Cl)Cl>[Cl:28][CH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:1][C:2]2[CH:7]=[C:6]([C:8]3[S:9][CH:10]=[CH:11][CH:12]=3)[CH:5]=[CH:4][C:3]=2[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:35])=[CH:32][CH:31]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a suspension of amine 4 (0.45 g, 1.55 mmol) in DCM (6.84 mL), cooled to −20° C., was added triethylamine (0.65 mL, 4.65 mmol) followed by a solution of 4-(chloromethyl)benzoyl chloride 73 (0.322 g, 1.71 mmol) in DCM (2.28 mL) via canula. The cold bath was then removed and the reaction mixture was stirred at room temperature for 1 h, washed with saturated NH4Cl, saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated. The crude material was recrystallized from 30% AcOEt in hexane to give title compound 74 (0.431 g, 63% yield).

Workup

customThe cold bath was then removed
washwashed with saturated NH4Cl, saturated NaHCO3, brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude material was recrystallized from 30% AcOEt in hexane

Sources & evidence

ORD record: ord-8b3596d8753f4b91ae1ae2d9e7dc9eb8
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598168B2

Reaction notes

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