Diisopropylethylamine → HCID 15896093, compound

HRID 432588Notes

Reaction equation

HRID 432588 reaction equation
[C:1]([CH2:4][NH:5][C:6]([NH:8][CH2:9][C:10]1[CH:28]=[CH:27][C:13]([C:14]([N:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])=[CH:12][C:11]=1[CH3:29])=[O:7])([OH:3])=O.C[CH2:31][N:32](C(C)C)C(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.CN>ClCCl>[CH3:31][NH:32][C:1](=[O:3])[CH2:4][NH:5][C:6]([NH:8][CH2:9][C:10]1[CH:28]=[CH:27][C:13]([C:14]([N:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])=[CH:12][C:11]=1[CH3:29])=[O:7]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 6364545Methylamine hydrochlorideHCID 15896092HCID 15896092, compound

Product 1

HCID 15896093HCID 15896093, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the carboxylic acid from Example 6 (0.109, 0.25 mmol) in dichloromethane (25 ml) was added DIEA (0.221 ml, 1.26 mmol) and PyBroP (0.129 g, 0.278 mmol). The mixture was stirred at room temperature for 10 min and then methylamine hydrochloride (0.085 g, 1.26 mmol) was added. Stirring was continued for a further 3 h. The mixture was then washed with 1M KHSO4 (3 times), saturated sodium bicarbonate solution (3 times) and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica (eluant dichloromethane:methanol 96:4) to give a white solid; yield 0.018 g (17%).

Workup

  1. stirringStirring
  2. waitwas continued for a further 3 h
  3. washThe mixture was then washed with 1M KHSO4 (3 times), saturated sodium bicarbonate solution (3 times) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica (eluant dichloromethane:methanol 96:4)
  7. customto give a white solid

Sources & evidence

ORD record
ord-cfe1307873b948bcbc77930fceb3ddad
Source dataset
uspto-grants-2003_12
Patent number
US06664249B1

Reaction notes

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