Ammonia → HCID 86706046, compound

HRID 2405698Notes

Reaction equation

HRID 2405698 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]12[CH2:16][CH:15]3[CH2:17][C:11]([C:18]([OH:20])=O)([CH2:12][CH:13]1[CH2:14]3)[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:23](C(C)C)C(C)C.N.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]12[CH2:16][CH:15]3[CH2:17][C:11]([C:18](=[O:20])[NH2:23])([CH2:12][CH:13]1[CH2:14]3)[CH2:10]2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68293539HCID 68293539, compound

Product 1

HCID 86706046HCID 86706046, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3a-tert-Butoxycarbonylaminohexahydro-2,5-methanopentalene-2-carboxylic acid was dissolved in DMF (200 ml), and DIPEA (10.6 g) and ammonia (6.1 ml, 7M in MeOH) were added. Subsequently, HATU (14.8 g) was added and the mixture was stirred at room temperature for 2 h. The reaction solution was concentrated by rotary evaporation down to volume 50 ml, poured into 400 ml of dilute NaHCO3 solution (300 ml of H2O+100 ml of saturated NaHCO3 solution) and extracted 3 times with 100 ml of EtOAc. Then dried over MgSO4, filtered and concentrated by rotary evaporation.

Workup

  1. concentrationThe reaction solution was concentrated by rotary evaporation down to volume 50 ml
  2. additionpoured into 400 ml of dilute NaHCO3 solution (300 ml of H2O+100 ml of saturated NaHCO3 solution)
  3. extractionextracted 3 times with 100 ml of EtOAc
  4. dry with materialThen dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-62ec4f61114949d088a2c02b8fdf0d50
Source dataset
uspto-grants-2014_08
Patent number
US08809324B2

Reaction notes

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