Triethylamine → [3-(1-Pyridin-2-yl-cyclopropylcarbamoyl)-oxetan-3-yl]-carbamic acid tert-butyl ester

HRID 1040554Notes

Reaction equation

HRID 1040554 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]([OH:15])=O)[CH2:12][O:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1([NH2:25])[CH2:24][CH2:23]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.CO.O>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1([C:13](=[O:15])[NH:25][C:22]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=3)[CH2:24][CH2:23]2)[CH2:10][O:11][CH2:12]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 111054091-(Pyridin-2-yl)cyclopropanamineHCID 565929693-(Boc-amino)oxetane-3-carboxylic acid

Product 1

HCID 58430978[3-(1-Pyridin-2-yl-cyclopropylcarbamoyl)-oxetan-3-yl]-carbamic acid tert-butyl esterYield 104.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-tert-butoxycarbonylamino-oxetane-3-carboxylic acid (82 mg, 0.38 mmol), 1-pyridin-2-yl-cyclopropylamine (56 mg, 0.42 mmol), HATU (215 mg, 0.57 mmol), and triethylamine (77 μL, 0.57 mmol) in DMF (0.5 mL) was stirred at room temperature for 29 h. Water (0.2 mL) and MeOH (1 mL) were added, and the resulting clear solution was purified directly by reverse phase HPLC to give [3-(1-pyridin-2-yl-cyclopropylcarbamoyl)-oxetan-3-yl]-carbamic acid tert-butyl ester as a tan solid (132 mg, >100%) after lyophilization, m/z 334.8 [M+1]+, that was carried on without further purification.

Workup

  1. customthe resulting clear solution was purified directly by reverse phase HPLC

Sources & evidence

ORD record
ord-25782a931e5241428861fda2ab5132ec
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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