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Diisopropylethylamine → HCID 58504191, compound

HRID 2407814
Notes
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Reaction equation

HRID 2407814 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([OH:15])=O)[CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[NH2:48][CH2:49][C:50]1([CH3:63])[CH2:55][CH2:54][N:53]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:52][CH2:51]1>CN(C)C=O.O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:48][CH2:49][C:50]2([CH3:63])[CH2:55][CH2:54][N:53]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:52][CH2:51]2)=[O:15])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 118464604-Amino-5-cyano-6-ethoxypicolinic acidHCID 23282898tert-Butyl 4-(aminomethyl)-4-methylpiperidine-1-carboxylate

Product 1

HCID 58504191
HCID 58504191, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-amino-5-cyano-6-ethoxypicolinic acid (0.100 g) in N,N-dimethylformamide (2.5 mL) was treated with 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (0.102 g), 1-hyroxybenzotriazole hydrate (0.0813 g), followed by diisopropylethylamine (0.252 mL) at room temperature. After stirring for 15 minutes, the compound prepared in Example 416 (0.116 g) was added. Stirring was continued overnight, the mixture diluted with water, organic layer separated and washed with brine, dried, evaporated in vacuo to a beige paste that was triturated in ether and solids collected by filtration (0.584 g) with the following physical data.

Workup

  1. stirringStirring
  2. waitwas continued overnight
  3. customseparated
  4. washwashed with brine
  5. customdried
  6. customevaporated in vacuo to a beige paste that
  7. customwas triturated in ether
  8. filtrationsolids collected by filtration (0.584 g) with the following physical data

Sources & evidence

ORD record
ord-24ea73bac6ae4e5e95c1b6bf907e171d
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08809538B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes