Sodium Bicarbonate → HCID 71274179, compound

HRID 2175409Notes

Reaction equation

HRID 2175409 reaction equation
CON(C)[C:4]([C:6]1[S:7][C:8]([CH2:11][NH:12][C:13]2[CH:18]=[C:17]([O:19][CH2:20][C@H:21]3[CH2:23][C@@H:22]3[C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]=3)[N:16]=[C:15]([CH3:31])[N:14]=2)=[N:9][N:10]=1)=[O:5].C[Mg+].[Br-].[C:36](=O)(O)[O-].[Na+]>C1COCC1.C1(C)C=CC=CC=1>[CH3:31][C:15]1[N:14]=[C:13]([NH:12][CH2:11][C:8]2[S:7][C:6]([C:4](=[O:5])[CH3:36])=[N:10][N:9]=2)[CH:18]=[C:17]([O:19][CH2:20][C@H:21]2[CH2:23][C@@H:22]2[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]=2)[N:16]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 86729571HCID 86729571, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 71274179HCID 71274179, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the solution of N-methoxy-N-methyl-5-((2-methyl-6-(((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methoxy)pyrimidin-4-ylamino)methyl)-1,3,4-thiadiazole-2-carboxamide (17-1) (355 mg, 0.78 mmol) in THF (2 mL) was added CH3MgBr (1.3 mL, 3.90 mmol) in toluene dropwise at 0° C. The mixture was stirred for 30 min. Then the solution was adjusted to pH=9-10 with saturated sodium bicarbonate and extracted with ethyl acetate (20 mL*3). The organic layers were combined, dried over anhydrous sodium sulfate and purified by Prep TLC (PE/EA=1:1). The product was obtained as a white solid (248 mg, 77%). 1H NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 7.37 (d, J=7.6 Hz, 1H), 7.03 (d, J=7.9 Hz, 1H), 5.59 (s, 1H), 5.42 (s, 1H), 4.99 (d, J=6.3 Hz, 2H), 4.28 (m, 2H), 2.79 (s, 3H), 2.44 (s, 3H), 2.28 (s, 3H), 2.07 (m, 1H), 1.89-1.81 (m, 1H), 1.32-1.27 (m, 1H), 1.04-1.02 (m, 1H); LRMS (ES) calculated M+H for C20H23N6O2S: 411.5. Found:411.1.

Workup

  1. extractionextracted with ethyl acetate (20 mL*3)
  2. dry with materialdried over anhydrous sodium sulfate
  3. custompurified by Prep TLC (PE/EA=1:1)

Sources & evidence

ORD record
ord-80df0bb8872d4f2b832f9fd51641d306
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

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