Dimethylformamide → HCID 178486788, compound

HRID 1012151Notes

Reaction equation

HRID 1012151 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]([OH:17])=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[CH3:29][O:30][C:31]1[C:45]([O:46][CH3:47])=[CH:44][C:34]2[NH:35][C:36]([C:38]3[C:42]([NH2:43])=[CH:41][NH:40][N:39]=3)=[N:37][C:33]=2[CH:32]=1.C(N(C(C)C)CC)(C)C>C1COCC1.CO>[CH3:47][O:46][C:45]1[C:31]([O:30][CH3:29])=[CH:32][C:33]2[NH:37][C:36]([C:38]3[C:42]([NH:43][C:15]([CH:11]4[O:12][CH2:13][CH2:14][N:9]([CH2:2][C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=5)[CH2:10]4)=[O:17])=[CH:41][NH:40][N:39]=3)=[N:35][C:34]=2[CH:44]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 27763524-Benzylmorpholine-2-carboxylic acid hydrochlorideHCID 178486794HCID 178486794, compound

Product 1

HCID 178486788HCID 178486788, compoundYield 10.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of rac-4-benzyl-2-morpholinecarboxylic acid hydrochloride (77 mg, 0.30 mmol) in THF (2 ml) was added DMF (2.0 μl, 0.025 mmol) followed by oxalyl chloride (36 ul, 0.41 mmol). After stirring at room temperature for 20 min. the mixture was evaporated to dryness and then re-suspended in THF (2 ml). A solution of 3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (60 mg, 0.2 mmol) and diisopropylethylamine (110 μl, 0.9 mmol) in THF (1 ml) was then added and the reaction stirred for at room temperature for 1 h. After 1 h, MeOH (1 ml) was added, the mixture concentrated and the residue purified through preparative LC/MS to give N-[3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-rac-4-benzyl-2-morpholinecarboxamide (AT8769) as a white solid (10 mg, 9%). (LC/MS (basic method): Rt 2.86 min, [M+H]+ 463).

Workup

  1. customwas evaporated to dryness
  2. stirringthe reaction stirred for at room temperature for 1 h
  3. waitAfter 1 h
  4. concentrationthe mixture concentrated
  5. customthe residue purified through preparative LC/MS

Sources & evidence

ORD record
ord-61ef1b4438d5482c8fa343a52267a128
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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