Diisopropylethylamine → HCID 18536554, compound

HRID 412587Notes

Reaction equation

HRID 412587 reaction equation
[C:1]([C:3]1([CH2:15][CH2:16][O:17][C:18]2[CH:27]=[C:26]3[C:21]([CH2:22][CH2:23][NH:24][CH2:25]3)=[CH:20][CH:19]=2)[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)#[N:2].C(N(C(C)C)CC)(C)C.[ClH:37].[N:38]1([C:43](N)=[NH:44])C=CC=N1>CN(C)C=O>[ClH:37].[ClH:37].[C:1]([C:3]1([CH2:15][CH2:16][O:17][C:18]2[CH:27]=[C:26]3[C:21]([CH2:22][CH2:23][N:24]([C:43]([NH2:44])=[NH:38])[CH2:25]3)=[CH:20][CH:19]=2)[CH2:4][CH2:5][N:6]([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[CH2:7][CH2:8]1)#[N:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 18536388HCID 18536388, compound

Product 1

HCID 18536554HCID 18536554, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-[2-[4-cyano-1-(pyridin-4-yl)piperidin-4-yl]ethoxy]-1,2,3,4-tetrahydroisoquinoline (70 mg) in dimethylformamide (5 ml)solution were added diisopropylethylamine (0.1 ml) and 1H-pyrazole-1-carboxamidine hydrochloride (85 mg), and the mixture was stirred at room temperature for 15 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was purified by HPLC (0.05% aquesous trifluoroacetic acid:methanol=1:1). The obtained residue was treated with dil. hydrochloric acid and dried under reduced pressure to give the title compound (67 mg).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. customthe obtained residue was purified by HPLC (0.05% aquesous trifluoroacetic acid:methanol=1:1)
  4. additionThe obtained residue was treated with dil. hydrochloric acid
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-54df17d6683d465dbce961a3b17b37e1
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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