Triethylamine → HCID 178436378, compound

HRID 75500Notes

Reaction equation

HRID 75500 reaction equation
Cl.[CH2:2]([C:4]1[CH:8]=[C:7]([CH2:9][CH3:10])[N:6]([CH2:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([NH2:18])[CH2:14][CH2:13]2)[N:5]=1)[CH3:3].C(N(CC)CC)C.[Cl:26][C:27]1[CH:28]=[N:29][C:30]([CH3:36])=[C:31]([CH:35]=1)[C:32](Cl)=[O:33]>C(Cl)Cl>[Cl:26][C:27]1[CH:28]=[N:29][C:30]([CH3:36])=[C:31]([CH:35]=1)[C:32]([NH:18][C@H:15]1[CH2:14][CH2:13][C@H:12]([CH2:11][N:6]2[C:7]([CH2:9][CH3:10])=[CH:8][C:4]([CH2:2][CH3:3])=[N:5]2)[CH2:17][CH2:16]1)=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 532566655-Chloro-2-methylnicotinoyl chloride2×HCID 178436377HCID 178436377, compound2×

Product 1

HCID 178436378HCID 178436378, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans-4-(3,5-diethyl-pyrazol-1-ylmethyl)-cyclohexylamine hydrochloride (Intermediate B) (65 mg, 0.238 mmol) was placed in a flask with DCM (5 ml) and triethylamine (72 mg, 0.714 mmol). 5-Chloro-2-methylnicotinoyl chloride (Intermediate C) (54 mg, 0.238 mmol) was added portionwise. After addition of the acid chloride, the reaction mixture was stirred at RT for 1 hour and partitioned between DCM and sat. NaHCO3. The organic phase was passed through a phase separator and the solvent was removed in vacuo. The crude product was triturated in EtOAc:iso-hexane—1:1, filtered and dried to afford the title compound; 1H NMR (d6-DMSO, 400 MHz) δ 8.52 (1H, d), 8.39 (1H, d), 7.79 (1H, d), 5.82 (1H, s), 3.76 (2H, d), 3.67 (1H, m), 2.57 (2H, q), 2.47 (5H, m), 1.89 (2H, m), 1.72 (1H, m), 1.57 (2H, m), 1.23 (10H, m); LC-MS Rt 2.35 mins, [M+H]+ 389; Method LowpH_v002.

Workup

  1. custompartitioned between DCM and sat. NaHCO3
  2. customthe solvent was removed in vacuo
  3. customThe crude product was triturated in EtOAc
  4. filtrationiso-hexane—1:1, filtered
  5. customdried

Sources & evidence

ORD record
ord-a4aba3a9724f4541984e774ba4f80c69
Source dataset
uspto-grants-2014_09
Patent number
US08835444B2

Reaction notes

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