Water → HCID 49788628, compound

HRID 2383002Notes

Reaction equation

HRID 2383002 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2N(O)N=N[C:5]=2[CH:6]=1.[NH3:11].CN(C(ON1N=[N:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26]C1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CC[N:36]([CH:40]([CH3:42])C)[CH:37]([CH3:39])C.[OH2:43].[CH3:44]N(C=O)C>>[CH:5]1([C:44]2[NH:11][C:25]([C:26]3[CH:39]=[CH:37][N:36]=[CH:40][CH:42]=3)=[CH:24][C:23]=2[C:22]([NH2:27])=[O:43])[CH2:4][CH2:3][CH2:2][CH2:1][CH2:6]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 1131751H-Benzotriazol-1-ol--ammonia (1/1)HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 49788628HCID 49788628, compoundYield 43%

Procedure

A solution of acid 7 (0.3 g, 1 mmol), HOBT-NH3 (0.3 g, 2 mmol), TBTU (0.64 g, 2 mmol), DIEA (1 mL, 6 mmol) in DMF (4 mL) was stirred at rt for 6 h. The reaction mixture was poured into water and the aqueous phase was extracted (×3) with EtOAc. The organic phase was washed with 1N NaOH, then with water, brine, dried (Na2SO4) and concentrated. The crude material was purified by silica gel chromatography (DCM/MeOH 12:1) to yield 2-cyclohexyl-5-pyridin-4-yl-1H-pyrrole-3-carboxylic acid amide (0.12 g, 43%) as a white solid.

Workup

  1. extractionthe aqueous phase was extracted (×3) with EtOAc
  2. washThe organic phase was washed with 1N NaOH
  3. dry with materialwith water, brine, dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude material was purified by silica gel chromatography (DCM/MeOH 12:1)

Sources & evidence

ORD record
ord-d76b3e3d49b541dabb4ed35d045f2eae
Source dataset
uspto-grants-2012_09
Patent number
US08263604B2

Reaction notes

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