Diisopropylethylamine → HCID 10311242, compound

HRID 23723Notes

Reaction equation

[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20]Cl)=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.Cl.Cl.[CH3:28][NH:29][CH2:30][C@H:31]([C:33]1[N:38]=[CH:37][CH:36]=[CH:35][N:34]=1)[OH:32].C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20][N:29]([CH2:30][C@@H:31]([OH:32])[C:33]4[N:34]=[CH:35][CH:36]=[CH:37][N:38]=4)[CH3:28])=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of N-(4-fluorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (216 mg, 0.570 mmol), (1R)-2-(methylamino)-1-pyrimidin-2-ylethanol dihydrochloride (Preparation 104, 155 mg, 0.686 mmol) and diisopropylethylamine (600 μL, 3.44 mmol) in dry DMF (10.0 mL) was stirred at 60° C. for 20 hours. The solution was then diluted with water (75 mL). The resulting precipitate was collected by filtration and the collected solid was dried at 60° C. in vacuo, providing 209 mg of a tan solid.

Workup

filtrationThe resulting precipitate was collected by filtration
customthe collected solid was dried at 60° C. in vacuo

Sources & evidence

ORD record: ord-6d90b16ce8b84458b80f9a5556655209
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852731B2

Reaction notes

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