Diisopropylethylamine → HCID 69621153, compound

HRID 1047128Notes

Reaction equation

HRID 1047128 reaction equation
[CH2:1]([NH:3][C:4](=[O:43])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:19](=[N:20][CH:21]=2)[N:18]([C@@H:22]2[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]2)[CH:17]=[C:16]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:15]3=[O:33])=[C:8]([C:34]2[S:35][CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[N:38]=2)[CH:7]=1)[CH3:2].FC(F)(F)C(O)=O.[O:51]1[CH2:56][CH2:55][N:54]([CH2:57][CH:58]=O)[CH2:53][CH2:52]1.CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH2:1]([NH:3][C:4](=[O:43])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:19](=[N:20][CH:21]=2)[N:18]([C@@H:22]2[CH2:27][CH2:26][CH2:25][N:24]([CH2:58][CH2:57][N:54]4[CH2:55][CH2:56][O:51][CH2:52][CH2:53]4)[CH2:23]2)[CH:17]=[C:16]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:15]3=[O:33])=[C:8]([C:34]2[S:35][CH:36]=[C:37]([C:39]([F:40])([F:42])[F:41])[N:38]=2)[CH:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 69621152HCID 69621152, compoundHCID 86665037HCID 86665037, compound

Product 1

HCID 69621153HCID 69621153, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxo-1-(piperidin-3-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Example 27, 0.050 g, 0.08 mmol) was taken up in THF (2 mL) and 2-morpholinoacetaldehyde 2,2,2-trifluoroacetate (0.024 g, 0.10 mmol) and DIEA (0.043 mL, 0.24 mmol) were added. The mixture was stirred at RT for 15 min. then sodium triacetoxyborohydride (0.078 g, 0.37 mmol) was added and reaction was stirred at RT for 6 hrs. The reaction was then quenched with NaHCO3 and extracted with DCM three times. Organics were combined and dried over Na2SO4 then the solvent was removed in vacuo. The residue was purified by flash column chromatography on silica gel using (dichloromethane-methanol) to give (R)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(1-(2-morpholinoethyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (0.026 mg, 44%).

Workup

  1. customreaction
  2. stirringwas stirred at RT for 6 hrs
  3. customThe reaction was then quenched with NaHCO3
  4. extractionextracted with DCM three times
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel using (dichloromethane-methanol)

Sources & evidence

ORD record
ord-3709715e251c4113941c7466c20369b8
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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