Triethylamine → HCID 46852210, compound

HRID 241662Notes

Reaction equation

HRID 241662 reaction equation
[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([CH2:17][CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)(=[O:16])=[O:15])=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26].C(N(CC)CC)C.[NH:37]1[CH:41]=[C:40]([C:42](O)=[O:43])[CH:39]=[N:38]1>ClCCl>[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([CH2:17][CH:18]3[CH2:19][CH2:20][N:21]([C:42]([C:40]4[CH:41]=[N:37][NH:38][CH:39]=4)=[O:43])[CH2:22][CH2:23]3)(=[O:16])=[O:15])=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:24][C:25]([CH3:26])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3015937Pyrazole-4-carboxylic acidHCID 58513618HCID 58513618, compound

Product 1

HCID 46852210HCID 46852210, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N,N-dimethyl-2-(2-neopentyl-5-(piperidin-4-ylmethylsulfonyl)-1H-benzo[d]imidazol-1-yl) ethanamine (STEP C, 687 mg, 1.63 mmol) in dichloromethane (8 mL) were added triethylamine (230 microL, 1.63 mmol), 1H-pyrazole-4-carboxylic acid (201 mg, 1.80 mmol) and O-benzo-triazole-N,N,N′,N′-tetramethyl-uronium-hexafluoro-phosphate (638 mg, 1,68 mmol) at room temperature. After 2 h, the mixture was diluted with dichloromethane (80 mL) and washed with sodium bicarbonate aqueous solution and brine. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by amine gel column chromatography (ethyl acetate-methanol, gradient) to give the title compound (757 mg, 90%) as a pale yellow grease.

Workup

  1. washwashed with sodium bicarbonate aqueous solution and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by amine gel column chromatography (ethyl acetate-methanol, gradient)

Sources & evidence

ORD record
ord-ee27fd449977469c9265e2d4c1657937
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

Loading…