2-Amino-1-butanol, (-)- → 5-[N-[(1R)-1-ethyl-2-hydroxyethyl]carbamoyl]-2-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]pyridine

HRID 381355Notes

Reaction equation

HRID 381355 reaction equation
[CH:1]([NH:4][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][N:20]=3)=[O:18])[CH2:13][CH2:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].[NH2:28][C@H:29]([CH2:32][CH3:33])[CH2:30][OH:31]>>[CH2:32]([C@@H:29]([NH:28][C:23]([C:22]1[CH:26]=[CH:27][C:19]([C:17]([N:14]2[CH2:13][CH2:12][N:11]([C:6]3[C:5]([NH:4][CH:1]([CH3:2])[CH3:3])=[CH:10][CH:9]=[CH:8][N:7]=3)[CH2:16][CH2:15]2)=[O:18])=[N:20][CH:21]=1)=[O:24])[CH2:30][OH:31])[CH3:33]

Participants

3

Reactant 2

HCID 27238562-Amino-1-butanol, (-)-HCID 183628186-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid

Product 1

HCID 99329435-[N-[(1R)-1-ethyl-2-hydroxyethyl]carbamoyl]-2-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]pyridineYield 83%

Procedure

By the same procedure as described in the example 1, synthesis was carried out starting with 6-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid and using (R)-(−)-2-amino-1-butanol. Then, the product was recrystallized with ethanol and petroleum ether to give a desired compound.

Workup

  1. customBy the same procedure as described in the example 1, synthesis
  2. customThen, the product was recrystallized with ethanol and petroleum ether

Sources & evidence

ORD record
ord-a442db1eda524530a9dbcc660cf82b87
Source dataset
uspto-grants-2001_10
Patent number
US06306860B1

Reaction notes

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