1-Propanamine, 3,3'-[1,4-butanediylbis(oxy)]bis- → HCID 86679316, compound

HRID 469274Notes

Reaction equation

HRID 469274 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=2)[CH:3]=1.[CH2:20]([O:29][CH2:30][CH2:31][CH2:32][NH2:33])[CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][NH2:28]>CCOC(C)=O>[NH2:33][CH2:32][CH2:31][CH2:30][O:29][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][NH:28][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 817291-Propanamine, 3,3'-[1,4-butanediylbis(oxy)]bis-HCID 86679317HCID 86679317, compound

Product 1

HCID 86679316HCID 86679316, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-(6-chloro-2-(methylthio)pyrimidin-4-ylamino)nicotinic acid (280 mg) and 3,3′-(butane-1,4-diylbis(oxy))dipropan-1-amine (1928 mg) was heated at 100° C. for 16 hours. After cooling to room etmperature, the mixture was diluted with EtOAc (200 mL), washed with H2O (100 mL), brine (100 mL), and dried over MgSO4 and concentrated. The residue was purified by preparative HPLC to give 6-(6-(3-(4-(3-aminopropoxy)butoxy)propylamino)-2-(methylthio)pyrimidin-4-ylamino)nicotinic acid (40 mg).

Workup

  1. temperatureAfter cooling to room etmperature
  2. washwashed with H2O (100 mL), brine (100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-ce3e345bc5d84b60878482e8c14c933c
Source dataset
uspto-grants-2014_01
Patent number
US08629150B2

Reaction notes

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