Isopropylamine → HCID 178457874, compound

HRID 1257645Notes

Reaction equation

HRID 1257645 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[C:5]([O:9][C:10]([NH:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([OH:21])=O)[CH2:15][CH2:14]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:5]([O:9][C:10](=[O:11])[NH:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([C:19](=[O:21])[NH:4][CH:1]([CH3:3])[CH3:2])[CH2:17][CH2:18]1)([CH3:6])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178453972HCID 178453972, compound

Product 1

HCID 178457874HCID 178457874, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Isopropylamine (925 μL, 10.86 mmol) was added to a stirred solution of trans 4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (1.32 g, 5.43 mmol), HATU (2.06 g, 5.43 mmol) and diisopropylethylamine (2.79 mL, 16.3 mmol) in DMF (50 ml). The resulting mixture was stirred at ambient temperature for 72 hours. The solvent was evaporated under vacuum and the residues diluted with water and extracted into DCM. The combined organic extracts were washed with 1M sodium hydroxide, water and brine, dried with magnesium sulfate and concentrated under vacuum affording 1.37 g (89%) of trans (4-isopropylcarbamoyl-cyclohexyl)-carbamic acid tert-butyl ester as a white solid. LCMS (Method B, ESI): RT=3.07 min, m+H+ MeCN=326.3; 1H NMR (400 MHz, DMSO) δ: 7.50 (d; 1H); 6.66 (d; 1H); 3.78 (m; 1H); 3.13 (m; 1H); 1.94 (m; 1H); 1.78 (d; 2H); 1.66 (d; 2H); 1.37 (s; 9H); 1.31 (m; 2H); 1.11 (m; 2H); 1.01 (d; 6H).

Workup

  1. customThe solvent was evaporated under vacuum
  2. additionthe residues diluted with water
  3. extractionextracted into DCM
  4. washThe combined organic extracts were washed with 1M sodium hydroxide, water and brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0de1ac9509d344b585e306fe9f4b10a4
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

Loading…