Triethylamine → HCID 71114400, compound

HRID 57610Notes

Reaction equation

HRID 57610 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:22]=[C:21]([N:23]4[CH2:27][CH2:26][C@@H:25]([CH2:28][NH2:29])[CH2:24]4)[C:20]4[C:15](=[N:16][CH:17]=[CH:18][N:19]=4)[CH:14]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.CCN(CC)CC.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>C1COCC1>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:22]=[C:21]([N:23]4[CH2:27][CH2:26][C@@H:25]([CH2:28][NH:29][S:38]([CH3:37])(=[O:40])=[O:39])[CH2:24]4)[C:20]4[C:15](=[N:16][CH:17]=[CH:18][N:19]=4)[CH:14]=3)=[CH:9][CH:8]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 71113335(S)-(1-(7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yl)pyrrolidin-3-yl)methanamine2×

Product 1

HCID 71114400HCID 71114400, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under N2, to a solution of (S)-(1-(7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yl)pyrrolidin-3-yl)methanamine (Compound 77, 51 mg, 0.13 mmol) and Et3N (0.04 mL, 0.26 mmol) in anhydrous THF (3 mL) was added MsCl (30 mg, 0.26 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 0.5 hour, then quenched with H2O and extracted with EtOAc. The combined extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by preparative thin-layer chromatography to afford the title compound. MS (m/z): 469 (M+H)+.

Workup

  1. customquenched with H2O
  2. extractionextracted with EtOAc
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-172ba8afdfe145bc82aec26d7c10b606
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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