Potassium tert-butoxide → HCID 56953402, compound

HRID 712303Notes

Reaction equation

HRID 712303 reaction equation
[CH2:1]([NH:3][C:4](=[O:40])[NH:5][C:6]1[S:7][C:8]2[C:14]([C:15](C3SC=CN=3)=[O:16])=[CH:13][C:12]([C:22]3[CH:23]=[N:24][C:25]([N:28]4[CH2:33][CH2:32][C:31]([CH3:39])([C:34]([O:36]CC)=[O:35])[CH2:30][CH2:29]4)=[N:26][CH:27]=3)=[CH:11][C:9]=2[N:10]=1)[CH3:2].C[C:42]([CH3:45])([O-])C.[K+]>CS(C)=O>[CH2:1]([NH:3][C:4]([NH:5][C:6]1[S:7][C:8]2[C:14]([C:15](=[O:16])[NH:10][C:6]3[S:7][CH:42]=[CH:45][N:5]=3)=[CH:13][C:12]([C:22]3[CH:23]=[N:24][C:25]([N:28]4[CH2:29][CH2:30][C:31]([CH3:39])([C:34]([OH:36])=[O:35])[CH2:32][CH2:33]4)=[N:26][CH:27]=3)=[CH:11][C:9]=2[N:10]=1)=[O:40])[CH3:2]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86664017HCID 86664017, compound

Product 1

HCID 56953402HCID 56953402, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Ethyl 1-(5-(2-(3-ethylureido)-7-(thiazole-2-carbonyl)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate (185 mg, 0.31 mmol) was dissolved in DMSO (2 ml) with stirring and potassium-t-butoxide (174 mg, 1.56 mmol) was added. The reaction was allowed to stir at rt for 1 h. The reaction was filtered and purified by preparative HPLC to afford Compound 145 as a solid (7 mg, 95% purity by HPCL) (4%) 1H NMR (DMSO-d6): δ 9.00-8.95 (2H, m), 8.63 (1H, s), 8.19 (1H, s), 7.65 (1H, d, J=3.59 Hz), 7.37 (1H, d, J=3.57 Hz), 6.93 (1H, t, J=5.58 Hz), 4.34 (2H, dt, J=13.73, 4.50 Hz), 3.41 (2H, dd, J=11.79, 3.40 Hz), 3.25 (2H, p, J=6.76 Hz), 2.06 (2H, dt, J=13.53, 3.67 Hz), 1.44 (2H, ddd, J=13.50, 9.94, 4.01 Hz), 1.23 (3H, s), 1.15 (3H, t, J=7.18 Hz). MS: 567 [M+H]+.

Workup

  1. stirringto stir at rt for 1 h
  2. filtrationThe reaction was filtered
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-9e2a574fb2604e0b8b00d157770bc5fe
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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