Triethylamine → HCID 57515693, compound

HRID 480430Notes

Reaction equation

HRID 480430 reaction equation
C([O:4][CH2:5][C:6](Cl)=[O:7])(=O)C.N[C@@H:10]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:11][NH:12][C:13]1[N:18]([CH3:19])[C:17](=[O:20])[C:16]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[C:15]([C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)[N:14]=1.C([N:43](CC)CC)C>ClCCl>[F:27][C:24]1[CH:23]=[CH:22][C:21]([C:16]2[C:17](=[O:20])[N:18]([CH3:19])[C:13]([NH:12][CH2:11][CH2:10][C@H:34]([NH:43][C:6](=[O:7])[CH2:5][OH:4])[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[N:14][C:15]=2[C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 15463810HCID 15463810, compound

Product 1

HCID 57515693HCID 57515693, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetoxyacetyl chloride (55 μl, 0.51 mmol) was added at ice-bath temperature to a stirring solution of 2-(((S)-2-amino-3-phenylpropyl)-amino)-5-(4-fluoro phenyl)-3-methyl-6-(4-pyridyl)-4(3H)-pyrimidinone (200 mg, 0.466 mmol) and triethylamine (130 μl, 0.93 mmol) in dichloromethane (4 ml). After 50 min, the reaction was quenched by the addition of a drop of methanol followed by evaporation. The resultant material was taken up in a 1:1:1 mixture of methanol/water/triethylamine (3 ml) and left overnight. Evaporation and subsequent column chromatography (3-7% methanol/chloroforme) provided the title compound. MS (m/z): 488.3 (M+H)+; C27H26FN5O3requir. 487.5.

Workup

  1. customthe reaction was quenched by the addition of a drop of methanol
  2. customfollowed by evaporation
  3. additionThe resultant material was taken up in a 1:1:1 mixture of methanol/water/triethylamine (3 ml)
  4. waitleft overnight
  5. customEvaporation and subsequent column chromatography (3-7% methanol/chloroforme)

Sources & evidence

ORD record
ord-5b494181d32d48eb92e1998bb6d1f47c
Source dataset
uspto-grants-2003_11
Patent number
US06649604B2

Reaction notes

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