Water → HCID 57925845, compound

HRID 1013508Notes

Reaction equation

HRID 1013508 reaction equation
Cl.[CH3:2][P:3]([CH2:6][CH2:7][NH2:8])([CH3:5])=[O:4].Br[CH2:10][C:11]1[CH:39]=[CH:38][C:14]([C:15]([NH:17][C:18]2[CH:19]=[C:20]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:21]=[CH:22][C:23]=2[NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:16])=[CH:13][CH:12]=1.CCN(C(C)C)C(C)C.O>CN(C=O)C.C([O-])(O)=O.[Na+]>[C:27]([O:26][C:25](=[O:31])[NH:24][C:23]1[CH:22]=[CH:21][C:20]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:19][C:18]=1[NH:17][C:15](=[O:16])[C:14]1[CH:38]=[CH:39][C:11]([CH2:10][NH:8][CH2:7][CH2:6][P:3]([CH3:5])([CH3:2])=[O:4])=[CH:12][CH:13]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 873542581003315-34-1HCID 91145363HCID 91145363, compound

Product 1

HCID 57925845HCID 57925845, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-(Dimethylphosphoryl)ethanamine hydrochloride (393 mg, 2.493 mmol), tert-butyl (3-{[4-(bromomethyl)benzoyl]amino}biphenyl-4-yl)carbamate (400 mg, 0.831 mmol), and DIEA (581 μl, 3.32 mmol) were combined in DMF (8 mL) and water (0.50 mL) and stirred at 60° C. overnight. The solution was diluted with saturated NaHCO3 and extracted with EtOAc (4×). The combined organics were dried (MgSO4), evaporated, and purified by reverse phase HPLC (25-95% MeCN/water w/0.025% TFA). Product fractions were neutralized with saturated NaHCO3, extracted with EtOAc (2×), dried (MgSO4), and evaporated to give a colorless solid.

Workup

  1. extractionextracted with EtOAc (4×)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. customevaporated
  4. custompurified by reverse phase HPLC (25-95% MeCN/water w/0.025% TFA)
  5. extractionextracted with EtOAc (2×)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give a colorless solid

Sources & evidence

ORD record
ord-0523f184d3714da588234b2ca9f36b31
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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