Triethylamine → HCID 86691171, compound

HRID 333085Notes

Reaction equation

HRID 333085 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=[N:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([N:39](CC)CC)C.[O:44]1C2N=CC=C(N)C=2C=[CH:45]1>C(#N)C>[O:44]1[C:26]2[C:27](=[N:28][CH:23]=[CH:24][C:25]=2[NH:39][C:10](=[O:12])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH:22]=[CH:45]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66835473HCID 66835473, compound

Product 1

HCID 86691171HCID 86691171, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(tert-butoxycarbonylamino)acetic acid (660 mg, 3.77 mmol) in acetonitrile (20 ml) was added HBTU (1.491 g, 3.93 mmol) and the resulting solution was stirred 40 minutes at room temperature. Then triethylamine (0.785 ml, 5.63 mmol) was added and the mixture was stirred another five minutes at room temperature. Next furo[2,3-b]pyridin-4-amine (253 mg, 1.886 mmol) was added and the reaction mixture was stirred at 60° C. over night. The acetonitrile was removed under reduced pressure and the residue was redissolved in dichloromethane (50 ml). The solution in dichloromethane was washed with aqueous 1N NaOH (40 ml). The aqueous phase was extracted with dichloromethane (2×15 ml), the combined organic phases were dried over sodium sulfate and concentrated under reduced pressure to yield 1.03 g of a slightly brown oil. The crude product was purified by column chromatography (silica gel using a gradient of 2 to 6% MeOH in DCM to yield 350 mg of a white foam (1.2 mmol, 64%). MS (ESI) m/z=292.2 [M+1]+.

Workup

  1. stirringthe mixture was stirred another five minutes at room temperature
  2. stirringthe reaction mixture was stirred at 60° C. over night
  3. customThe acetonitrile was removed under reduced pressure
  4. dissolutionthe residue was redissolved in dichloromethane (50 ml)
  5. washThe solution in dichloromethane was washed with aqueous 1N NaOH (40 ml)
  6. extractionThe aqueous phase was extracted with dichloromethane (2×15 ml)
  7. dry with materialthe combined organic phases were dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto yield 1.03 g of a slightly brown oil
  10. customThe crude product was purified by column chromatography (silica gel using a gradient of 2 to 6% MeOH in DCM

Sources & evidence

ORD record
ord-431d5b203570461fbc2483ab24636d9f
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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