Serinol → 5-[N-[Bis(hydroxymethyl)methyl]carbamoyl]-2-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]pyridine

HRID 381357Notes

Reaction equation

HRID 381357 reaction equation
CO[C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[C:23]([NH:24][CH:25]([CH3:27])[CH3:26])=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:14][CH2:13]2)=[O:11])=[N:6][CH:5]=1.[NH2:29][CH:30]([CH2:33][OH:34])[CH2:31][OH:32]>>[OH:32][CH2:31][CH:30]([CH2:33][OH:34])[NH:29][C:3]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:13][CH2:14][N:15]([C:18]3[C:23]([NH:24][CH:25]([CH3:27])[CH3:26])=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:16][CH2:17]2)=[O:11])=[N:6][CH:5]=1)=[O:28]

Participants

3

Reactant 2

HCID 68294SerinolHCID 109378486-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid methyl ester

Product 1

HCID 98246255-[N-[Bis(hydroxymethyl)methyl]carbamoyl]-2-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]pyridineYield 78%

Procedure

By the same procedure as described in the example 2, synthesis was carried out starting with 6-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid methyl ester and using 2-amino-1,3-propandiol. Then, the product was recrystallized with ethyl acetate and hexane to give a desired compound.

Workup

  1. customBy the same procedure as described in the example 2, synthesis
  2. customThen, the product was recrystallized with ethyl acetate and hexane

Sources & evidence

ORD record
ord-7b102423714244ad949f44964a3315f7
Source dataset
uspto-grants-2001_10
Patent number
US06306860B1

Reaction notes

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