Ammonia → HCID 49788628, compound

HRID 1400182Notes

Reaction equation

HRID 1400182 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[C:22]2[CH:23]=C[CH:25]=[CH:26][C:21]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CC[N:36]([CH:40]([CH3:42])C)[CH:37]([CH3:39])C.C[N:44]([CH:46]=[O:47])C>O>[CH:5]1([C:23]2[NH:11][C:26]([C:25]3[CH:39]=[CH:37][N:36]=[CH:40][CH:42]=3)=[CH:21][C:22]=2[C:46]([NH2:44])=[O:47])[CH2:4][CH2:3][CH2:2][CH2:1][CH2:6]1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 49788628HCID 49788628, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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-321b8b1d9a5a4e359e61bfc2f3bb5e1e
Source dataset
uspto-grants-2014_12
Patent number
US08906934B2

Reaction notes

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