1,3-Propanediamine, N1,N1,N3-trimethyl- → N,N,N'-Trimethyl-N'-[2-(5-phenyl-thiazol-2-ylamino)-pyridin-4-ylmethyl]-propane-1,3-diamine

HRID 1355510Notes

Reaction equation

HRID 1355510 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][N:14]=2)[CH:4]=1.[CH3:21][N:22]([CH3:28])[CH2:23][CH2:24][CH2:25][NH:26][CH3:27].C([O-])(O)=O.[Na+]>CS(C)=O>[CH3:21][N:22]([CH3:28])[CH2:23][CH2:24][CH2:25][N:26]([CH3:27])[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][N:14]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 516892Sodium BicarbonateHCID 11335641(4-Chloromethyl-pyridin-2-yl)-(5-phenyl-thiazol-2-yl)-amine

Product 1

HCID 18506881N,N,N'-Trimethyl-N'-[2-(5-phenyl-thiazol-2-ylamino)-pyridin-4-ylmethyl]-propane-1,3-diamine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(4-Chloromethyl-pyridin-2-yl)-(5-phenyl-thiazol-2-yl)-amine 8-8 (0.050 g, 0.166 mmol) was dissolved in 0.50 mL DMSO. N,N,N′-trimethyl-1,3-propanediamine was added and the reaction was stirred at RT. After 1 h a copious amount precipitate had formed. Saturated NaHCO3 (aq) was added and the resulting precipitate was filtered and washed with water to afford pure compound 8-9. 1H NMR (CDCl3) δ 9.16 (bs, 1H), 8.31 (d, 1H, J=5.1 Hz), 7.63 (s, 1H), 7.59 (d, 2H, J=7.4 Hz), 7.38 (t, 2H, J=7.6 Hz), 7.26 (overlapping with CHCl3), 6.91 (s, 1H), 6.88 (d, 1H, J=5.1 Hz), 3.49 (s, 2H), 2.43 (t, 2H, J=7.4 Hz), 2.30 (t, 2H, J=7.5 Hz), 2.34 (s, 3H), 2.21 (s, 6H), 1.68 (overlapping with water). MS [M+H]+382.3. mp 190-193.

Workup

  1. customAfter 1 h a copious amount precipitate had formed
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-7c97f14d6623442aa8466fc2e8fe37b1
Source dataset
uspto-grants-2003_07
Patent number
US06586424B2

Reaction notes

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