Dimethyl Sulfoxide → HCID 67445301, compound

HRID 1666072Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.[CH3:9]C(C)([O-])C.[K+].CS(C)=O.[C:19]([C:21]1[C:22]([NH:38][C:39]2[CH:40]=[C:41]([CH:46]=[CH:47][C:48]=2[CH3:49])[C:42]([NH:44][CH3:45])=[O:43])=N[C:24](S(C)(=O)=O)=[N:25][C:26]=1[N:27]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:28])#[N:20]>C(OCC)(=O)C>[C:19]([C:21]1[C:26]([N:27]([CH2:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH3:28])=[N:25][C:24]([O:8][CH:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:9][C:22]=1[NH:38][C:39]1[CH:40]=[C:41]([CH:46]=[CH:47][C:48]=1[CH3:49])[C:42]([NH:44][CH3:45])=[O:43])#[N:20]

Participants

Conditions

Temperature: 60 °C

Procedure

To a portion of 576 mg of 1-methylpiperidine-4-ol (576 mg; 5 mmol) is added 616 mg of potassium tert.-butoxide (5.5 mmol) followed by 4.0 mL of DMSO. After stirring this mixture at r.t. for 1 h a portion of 1.0 mL of this mixture is added at r.t. to 19 mg of 3-{5-cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-methanesulfonyl-pyrimidin-4-ylamino}-4,N-dimethyl-benzamide (0.043 mmol) on 0.2 mL of DMSO. The mixture was heated at 60° C. for 3 h. At r.t. 5 mL of ethyl acetate is added and the organic layer is washed with brine (1×4 mL). The organic layer is dried (MgSO4), volatiles are removed in vacuo and the product is purified via reversed phase prep. HPLC. (Yield: 18.6 mg; 0.026 mmol; 56%). MS (m/z): 480 (M+H).

Workup

customAt r.t
washthe organic layer is washed with brine (1×4 mL)
dry with materialThe organic layer is dried (MgSO4), volatiles
customare removed in vacuo
customthe product is purified via reversed phase prep

Sources & evidence

ORD record: ord-933458e793cb4d198d9a19b603486e26
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044040B2

Reaction notes

Loading…