Diisopropylethylamine → HCID 178510106, compound

HRID 474814Notes

Reaction equation

[N:1]1[CH:6]=[C:5]([CH2:7][C:8]2[C:9](=[O:15])[NH:10][C:11](=[S:14])[NH:12][CH:13]=2)[CH:4]=[N:3][CH:2]=1.CCN(C(C)C)C(C)C.[Cl:25][C:26]1[CH:42]=[CH:41][C:29]([O:30][C:31]2[CH:38]=[CH:37][C:36]([CH2:39]Cl)=[CH:35][C:32]=2[C:33]#[N:34])=[CH:28][C:27]=1[C:43]([F:46])([F:45])[F:44]>C(Cl)Cl>[Cl:25][C:26]1[CH:42]=[CH:41][C:29]([O:30][C:31]2[CH:38]=[CH:37][C:36]([CH2:39][S:14][C:11]3[NH:12][CH:13]=[C:8]([CH2:7][C:5]4[CH:6]=[N:1][CH:2]=[N:3][CH:4]=4)[C:9](=[O:15])[N:10]=3)=[CH:35][C:32]=2[C:33]#[N:34])=[CH:28][C:27]=1[C:43]([F:44])([F:45])[F:46]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 5-(5-pyrimidinylmethyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone (35.0 mg, 0.159 mmol) and DIPEA (0.08 mL, 0.458 mmol) in DCM (1 mL) was added 2-(4-chloro-3-(trifluoromethyl)phenoxy)-5-(chloromethyl)benzonitrile (50 mg, 0.144 mmol). The solution was heated at 60° C. overnight. Purification via MDAP then afforded the title compound (33 mg, 43.1% yield). LCMS: rt=3.28 min, [M+H+]=531

Workup

customPurification via MDAP

Sources & evidence

ORD record: ord-514a7be48c1f4fb49d3715f142a0503c
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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