1H-Imidazole-1-propanamine → 2-Bromo-N-[3-(1H-imidazol-1-yl)propyl]-5-thiazolecarboxamide

HRID 522698Notes

Reaction equation

HRID 522698 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:7]([OH:9])=O)=[CH:5][N:6]=1.[N:10]1([CH2:15][CH2:16][CH2:17][NH2:18])[CH:14]=[CH:13][N:12]=[CH:11]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>ClCCl>[N:10]1([CH2:15][CH2:16][CH2:17][NH:18][C:7]([C:4]2[S:3][C:2]([Br:1])=[N:6][CH:5]=2)=[O:9])[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

6

Reactant 4

HCID 787361H-Imidazole-1-propanamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27632102-Bromothiazole-5-carboxylic acid

Product 1

HCID 900133742-Bromo-N-[3-(1H-imidazol-1-yl)propyl]-5-thiazolecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

2-Bromothiazole-5-carboxylic acid (0.4 g, 1.923 mmol), 3-(1H-imidazole-1-yl)propan-1-amine (0.265 g, 2.115 mmol), and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) (0.935 g, 2.115 mmol) were mixed in dichloromethane (7 ml), treated with Hunig's base (0.705 ml, 4.04 mmol) and stirred at 25° C. for 2 hours. The reaction mixture was diluted with dichloromethane and washed with water and brine. The organic layer was dried (MgSO4), filtered and concentrated. Purification by flash chromatography (silica gel, 2-20% methanol/dichloromethane) afforded the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography (silica gel, 2-20% methanol/dichloromethane)

Sources & evidence

ORD record
ord-a99bcaaa48f845cf97ba0762728366ac
Source dataset
uspto-grants-2016_05
Patent number
US09334264B2

Reaction notes

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