Dimethylformamide → HCID 178501288, compound

HRID 1372773Notes

Reaction equation

HRID 1372773 reaction equation
CCN=C=N[CH2:6][CH2:7][CH2:8][N:9]([CH3:11])C.Cl.[CH:13]1[CH:14]=[CH:15][C:16]2N(O)N=N[C:17]=2[CH:18]=1.[Cl:23][C:24]1[C:25]([NH:35][C:36]([C:38]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:40]([CH3:47])[CH:39]=2)=[O:37])=[CH:26][C:27]([F:34])=[C:28]([CH2:30][C:31]([OH:33])=O)[CH:29]=1.[C:48]([O:51][CH2:52]C)(=[O:50])C.CN([CH:57]=[O:58])C>CN(C1C=CN=CC=1)C.[Cl-].[Na+].O>[Cl:23][C:24]1[C:25]([NH:35][C:36]([C:38]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:40]([CH3:47])[CH:39]=2)=[O:37])=[CH:26][C:27]([F:34])=[C:28]([CH2:30][C:31]([N:9]2[CH2:8][CH2:7][CH2:6][C@H:11]2[CH2:57][O:58][C@H:13]2[CH2:14][CH2:15][C@H:16]([C:48]([O:51][CH3:52])=[O:50])[CH2:17][CH2:18]2)=[O:33])[CH:29]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 17859070HCID 17859070, compound

Product 1

HCID 178501288HCID 178501288, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

In DMF (10 ml), EDC•HCl (274 mg, 1.43 mmol), DMAP (catalytic amount), and HOBt (catalytic amount) were added to (5-chloro-2-fluoro-4-((1-methyl-3-indolylcarbonyl)amino)phenyl)acetic acid (344 mg, 0.953 mmol) and methyl trans-4-((2S)-pyrrolidinylmethoxy)-1-cyclohexanecarboxylate (230 mg, 0.953 mmol) and the resulting mixture was stirred at room temperature for 15 hours. To the reaction mixture were added ethyl acetate (200 ml) and saturated brine (100 ml). The organic layer thus separated was washed with saturated brine (100 ml), dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. From chloroform-ethyl acetate (4:1) eluate fractions, methyl trans-4-(1((5-chloro-2-fluoro-4-(1-methyl-3-indolylcarbonylamino)phenyl)acetyl)-(2S)-pyrrolidinylmethoxy)-1-cyclohexanecarboxylate (556 mg, 100%) was obtained as a pale yellow oil.

Workup

  1. customThe organic layer thus separated
  2. washwas washed with saturated brine (100 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-58317ce52bab433385fdcd849bdf992b
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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