3-Aminopyridine → HCID 58767570, compound

HRID 1710453Notes

Reaction equation

HRID 1710453 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]1[CH2:25][N:14]2[C:15]3[CH:16]=[C:17]([C:22]([OH:24])=O)[CH:18]=[CH:19][C:20]=3[CH:21]=[C:13]2[C:12](=[O:26])[NH:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=[N:42][C:37]2[CH:38]=[CH:39][CH:40]=[N:41][C:36]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.NC1C=NC=CC=1>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C@@H:10]1[CH2:25][N:14]2[C:15]3[CH:16]=[C:17]([C:22](=[O:24])[NH:42][C:37]4[CH:36]=[N:41][CH:40]=[CH:39][CH:38]=4)[CH:18]=[CH:19][C:20]=3[CH:21]=[C:13]2[C:12](=[O:26])[NH:11]1)([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 5

HCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58767569HCID 58767569, compound

Product 1

HCID 58767570HCID 58767570, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of the above carboxylic acid (94 mg, 0.262 mmol) in 2 mL of DMF (2 mL) was added HATU (104.5 mg, 0.275 mmol), HOAt (18.6 mg, 0.137 mmol) and N,N′-diisopropylethylamine (96 uL, 0.55 mmol). After 15 min, 3-amino-pyridine (26 mg, 0.275 mmol) in 1 mL of DMF was added. The reaction mixture was warmed at 80° C. for 8 h. The reaction was concentrated and extracted with EtOAc several times. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated. Purification by silica gel chromatography gave 73 mg of [(R)-1-oxo-7-(pyridin-3-ylcarbamoyl)-1,2,3,4-tetrahydro-pyrazino[1,2-a]indol-3-ylmethyl]-carbamic acid tert-butyl ester, yield 64%. The product was characterized by 1H NMR and mass spectroscopy. ESI-MS m/z 436.48 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated
  2. extractionextracted with EtOAc several times
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-691503a51aa34a85b77e2b9ca36b760d
Source dataset
uspto-grants-2010_09
Patent number
US07790712B2

Reaction notes

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