Chloroacetone → HCID 67286623, compound

HRID 1753884Notes

Reaction equation

[CH2:1]([S:3][C:4]1[C:9]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[O:11])=[C:8]([CH3:21])[CH:7]=[C:6]([NH:22][CH3:23])[N:5]=1)[CH3:2].CCN(C(C)C)C(C)C.Cl[CH2:34][C:35](=[O:37])[CH3:36].[OH-].[Na+]>CN1C(=O)CCC1.CCOC(C)=O>[CH2:1]([S:3][C:4]1[C:9]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[O:11])=[C:8]([CH3:21])[CH:7]=[C:6]([N:22]([CH3:23])[CH2:34][C:35](=[O:37])[CH3:36])[N:5]=1)[CH3:2]

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 150 mg (0.45 mmol) 2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-6-(methyl-amino)-4-methyl-pyridine-3-carboxylic acid amide (synthesis is described in section a) of example 123) in NMP (1 ml) were added 229 μl (1.35 mmol) DIPEA and 39 μl (0.50 mmol) chloroacetone. The mixture was heated in the MW to 140° C. for 40 min and subsequently partiotionated between a 1M aq. NaOH sol and EtOAc. The organic layer was separated, washed with a 1M aq. NaOH sol, water and brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 13:7) provided 53 mg (0.14 mmol, 30%) 2-Ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methyl-6-[methyl-(2-oxo-propyl)-amino]-pyridine-3-carboxylic acid amide (example 253). [M+H]+390.2

Workup

customThe organic layer was separated
washwashed with a 1M aq. NaOH sol, water and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customPurification of the residue by CC (hexane/EtOAc 13:7)

Sources & evidence

ORD record: ord-3383269043d24c1eab109ae206b0b7c2
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09168259B2

Reaction notes

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