Triethylamine → HCID 67390883, compound

HRID 1040532Notes

Reaction equation

HRID 1040532 reaction equation
[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:2]([C:4]([OH:6])=O)[CH3:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[N:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[C:51]1([NH2:54])[CH2:53][CH2:52]1>CN(C=O)C.CCOC(C)=O>[C:10]([O:9][C:7](=[O:8])[NH:1][C@H:2]([C:4](=[O:6])[NH:54][C:51]1([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][N:45]=2)[CH2:53][CH2:52]1)[CH3:3])([CH3:13])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 85082Tert-butoxycarbonylalanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 111054091-(Pyridin-2-yl)cyclopropanamine

Product 1

HCID 67390883HCID 67390883, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Boc-Ala (100 mg, 0.53 mmol), HATU (261 mg, 0.69 mmol) and triethylamine (0.15 mL, 1.1 mmol) in DMF (2 mL) was added a solution of 1-pyridin-2-yl-cyclopropylamine (80 mg, 0.60 mmol) in DMF (1 mL). The mixture was stirred for 1.5 h then diluted with EtOAc (30 mL), washed with water (3×30 mL), brine (1×25 mL), dried with MgSO4, filtered, and concentrated to afford a crude solid. The crude material was purified by flash chromatography on silica gel, eluting with Hex/EtOAc (50/50 to 75/25) to afford [(S)-1-(1-pyridin-2-yl-cyclopropylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (120 mg, 74%) as a white solid.

Workup

  1. washwashed with water (3×30 mL), brine (1×25 mL)
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford a crude solid
  6. customThe crude material was purified by flash chromatography on silica gel
  7. washeluting with Hex/EtOAc (50/50 to 75/25)

Sources & evidence

ORD record
ord-e4d7788147c945f3a8cfb1e2b3cd5e6c
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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