Triethylamine → [1-(1-Pyrimidin-2-yl-cyclopropyl-carbamoyl)-3-1,2,3-triazol-2-yl-propyl]-carbamic acid tert-butyl ester

HRID 1040506Notes

Reaction equation

HRID 1040506 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][CH2:14][N:15]1[N:19]=[CH:18][CH:17]=[N:16]1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[N:22]1[CH:27]=[CH:26][CH:25]=[N:24][C:23]=1[C:28]1([NH2:31])[CH2:30][CH2:29]1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O.CCOC(C)=O>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([C:10](=[O:12])[NH:31][C:28]1([C:23]2[N:24]=[CH:25][CH:26]=[CH:27][N:22]=2)[CH2:30][CH2:29]1)[CH2:13][CH2:14][N:15]1[N:19]=[CH:18][CH:17]=[N:16]1)([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66897847HCID 66897847, compoundHCID 67390310HCID 67390310, compound

Product 1

HCID 67390356[1-(1-Pyrimidin-2-yl-cyclopropyl-carbamoyl)-3-1,2,3-triazol-2-yl-propyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the 2-tert-butoxycarbonylamino-4-1,2,3-triazol-2-yl-butyric acid (0.1 g, 0.37 mmol) in DMF (2 mL) was added 1-pyrimidin-2-yl-cyclopropylamine dihydrochloride (50 mg, 0.24 mmol) followed by Et3N (0.1 ml, 0.74 mmol) and HATU (211 mg, 0.55 mmol). The mixture was stirred at room temperature for 1 h. The mixture was diluted with water and EtOAc. The layers were separated and the organic layer was washed with water (3×30 mL), brine (2×30 mL), dried over MgSO4, filtered, and concentrated in vacuo to yield crude [1-(1-pyrimidin-2-yl-cyclopropyl-carbamoyl)-3-1,2,3-triazol-2-yl-propyl]-carbamic acid tert-butyl ester. The product was not purified and was used in subsequent reactions.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with water (3×30 mL), brine (2×30 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee581ea2ee0d4117a854e2a36d842e2c
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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