Diisopropylethylamine → HCID 23511635, compound

HRID 354166Notes

Reaction equation

HRID 354166 reaction equation
Cl.CN(C)CCCN=C=NCC.[I:13][C:14]1[CH:15]=[N:16][C:17]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:18]([CH:22]=1)[C:19]([OH:21])=O.[NH2:28][C:29]1[C:30]([CH2:41][CH3:42])=[N:31][N:32]([CH2:37][CH2:38][O:39][CH3:40])[C:33]=1[C:34]([NH2:36])=[O:35].O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>O1CCCC1>[NH2:36][C:34]([C:33]1[N:32]([CH2:37][CH2:38][O:39][CH3:40])[N:31]=[C:30]([CH2:41][CH3:42])[C:29]=1[NH:28][C:19](=[O:21])[C:18]1[CH:22]=[C:14]([I:13])[CH:15]=[N:16][C:17]=1[O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:35]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 115587965-iodo-2-butoxynicotinic acidHCID 23511608HCID 23511608, compound

Product 1

HCID 23511635HCID 23511635, compoundYield 133.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (434 mg, 2.26 mmol) was added to a stirred solution of 5-iodo-2-butoxynicotinic acid (615 mg, 1.92 mmol), 4-amino-3-ethyl-1-(2-methoxyethyl)-pyrazole-5-carboxamide (370 mg, 1.74 mmol), 1-hydroxybenzotriazole hydrate (346 mg, 2.26 mmol) and diisopropylethylamine (0.9 mL, 5.22 mmol) in tetrahydrofuran (12 mL) at room temperature under a nitrogen atmosphere. After 20 h the solvent was evaporated and the product was extracted from 10% sodium bicarbonate solution with dichloromethane (3×100 mL). The organics were dried (MgSO4) and concentrated to give a fawn solid. The solid was triturated with di-isopropylether to give an off-white solid (1.2 g).

Workup

  1. customAfter 20 h the solvent was evaporated
  2. extractionthe product was extracted from 10% sodium bicarbonate solution with dichloromethane (3×100 mL)
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated
  5. customto give a fawn solid
  6. customThe solid was triturated with di-isopropylether

Sources & evidence

ORD record
ord-ebf7f112f457401787de1d1d7e0e194a
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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