Ammonia → HCID 49788936, compound

HRID 1400185Notes

Reaction equation

HRID 1400185 reaction equation
CC[N:3]([CH:7](C)C)C(C)C.CC[N:12]=C=NCCCN(C)C.[CH:21]1[CH:22]=[CH:23][C:24]2[N:29](O)N=NC=2[CH:26]=1.N.[CH2:32]1[CH2:36][O:35][CH2:34][CH2:33]1>>[N:29]1[CH:26]=[CH:21][C:22]([C:36]2[NH:3][CH:7]=[C:33]([C:34]([NH2:12])=[O:35])[CH:32]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 49788936HCID 49788936, compoundYield 44%

Procedure

To a solution of acid 45 (137 mg, 0.61 mmol) in DIEA (213 μL, 1.22 mmol) and anhydrous THF (8 mL), cooled at 0° C., EDCI (175 mg, 0.09 mmol) and HOBT.NH3 (137 mg, 0.9 mmol) were added and the solution was stirred overnight at rt. The solution was concentrated, water was added and the product was extracted with DCM. The organic layer was washed with water, dried and concentrated to give a solid that was triturated with Et2O to afford 50 mg (44%) of 5-pyridin-4-yl-1H-pyrrole-3-carboxylic acid amide.

Workup

  1. concentrationThe solution was concentrated
  2. additionwater was added
  3. extractionthe product was extracted with DCM
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customto give a solid
  8. customthat was triturated with Et2O

Sources & evidence

ORD record
ord-f6507ed3f7334489a77031fd85f6e642
Source dataset
uspto-grants-2014_12
Patent number
US08906934B2

Reaction notes

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