Triethylamine → HCID 67132976, compound

HRID 545349Notes

Reaction equation

HRID 545349 reaction equation
[Na+].[CH:2]1([N:5]2[C:9]([C:10]([O-])=[O:11])=[C:8]([C:13]3[CH:14]=[N:15][C:16]([N:19]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:17][CH:18]=3)[N:7]=[C:6]2[C:34]2[CH:39]=[CH:38][C:37]([O:40][C:41]([F:44])([F:43])[F:42])=[CH:36][CH:35]=2)[CH2:4][CH2:3]1.[N:45]1([CH:50]2[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]2)[CH2:49][CH2:48][CH2:47][CH2:46]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:2]1([N:5]2[C:9]([C:10]([N:53]3[CH2:54][CH2:55][CH:50]([N:45]4[CH2:49][CH2:48][CH2:47][CH2:46]4)[CH2:51][CH2:52]3)=[O:11])=[C:8]([C:13]3[CH:14]=[N:15][C:16]([N:19]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:17][CH:18]=3)[N:7]=[C:6]2[C:34]2[CH:35]=[CH:36][C:37]([O:40][C:41]([F:44])([F:42])[F:43])=[CH:38][CH:39]=2)[CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 787034-(1-Pyrrolidinyl)piperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67133163HCID 67133163, compound

Product 1

HCID 67132976HCID 67132976, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.12 g (0.2 mmol) of 3-cyclopropyl-5-(6-dibenzylamino-pyridin-3-yl)-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid sodium salt and 0.03 g (0.2 mmol) of 4-pyrrolidin-1-yl-piperidine in 1 ml of DMF was added 83 microliters (0.6 mmol) of triethylamine and 0.08 g (0.2 mmol) of HATU. The mixture was stirred for 1 h after which time it was evaporated to dryness, the residue was partitioned between CH2Cl2 and saturated sodium hydrogen carbonate solution, the organic phase was dried with sodium sulfate and concentrated. Purification by flash column chromatography [MeOH/CH2Cl2 5:95] afforded 0.1 g (79%) of the title compound as a colorless solid. MS: 721.3 (MH+).

Workup

  1. customwas evaporated to dryness
  2. customthe residue was partitioned between CH2Cl2 and saturated sodium hydrogen carbonate solution
  3. dry with materialthe organic phase was dried with sodium sulfate
  4. concentrationconcentrated
  5. customPurification by flash column chromatography [MeOH/CH2Cl2 5:95]

Sources & evidence

ORD record
ord-21f54e94779b4d0e851c09d037bb251e
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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