Triethylamine → HCID 67001737, compound

HRID 1186246Notes

Reaction equation

HRID 1186246 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[CH:11]1([CH2:14][N:15]2[CH2:21][CH2:20][CH:19]3[CH2:22][NH:23][CH2:24][CH2:25][N:18]3[C:17]3[N:26]=[CH:27][CH:28]=[CH:29][C:16]2=3)[CH2:13][CH2:12]1.C(N(CC)CC)C>C(Cl)Cl>[CH:11]1([CH2:14][N:15]2[CH2:21][CH2:20][CH:19]3[CH2:22][N:23]([C:2]([C:3]4[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=4)=[O:9])[CH2:24][CH2:25][N:18]3[C:17]3[N:26]=[CH:27][CH:28]=[CH:29][C:16]2=3)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 67002159HCID 67002159, compound

Product 1

HCID 67001737HCID 67001737, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Nicotinoyl chloride hydrochloride (58.2 mg, 0.317 mmol) was added at room temperature to a solution of the product of Example 74A (82 mg, 0.317 mmol) in CH2Cl2 (4 mL) and triethylamine (0.111 mL, 0.793 mmol). The mixture was stirred at room temperature for 30 minutes and then concentrated under vacuum. The residue was purified by HPLC (30×100 mm, C18, Waters XBridge™ column eluted with 0.1 M aqueous (NH4)2CO3-methanol, 40:60-0:100 over 15 minutes) to provide the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 0.16-0.21 (m, 2H), 0.45-0.54 (m, 2H), 0.93-1.03 (m, 1H), 1.61-1.75 (m, 1H), 1.79-1.91 (m, 1H), 2.90-3.05 (m, 2H), 3.19-3.30 (m, 2H), 3.34-3.50 (m, 4H), 3.54-3.64 (m, 1H), 3.71-3.92 (m, 2H), 6.74 (dd, J=7.8, 4.7 Hz, 1H), 7.00 (dd, J=7.9, 1.5 Hz, 1H), 7.45 (ddd, J=7.9, 4.9, 0.9 Hz, 1H), 7.65 (dd, J=4.6, 1.5 Hz, 1H), 7.83 (ddd, J=8.1, 2.0, 1.8 Hz, 1H), 8.58-8.67 (m, 2H); MS (ESI) m/z 364 (M+H)+.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by HPLC (30×100 mm, C18, Waters XBridge™ column eluted with 0.1 M aqueous (NH4)2CO3-methanol, 40:60-0:100 over 15 minutes)

Sources & evidence

ORD record
ord-5e63ad54385b4517b0410b5cbcdae7fc
Source dataset
uspto-grants-2014_03
Patent number
US08673896B2

Reaction notes

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