Triethylamine → HCID 57814635, compound

HRID 521635Notes

Reaction equation

HRID 521635 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:21])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[CH:7][C:6]=1[C:22]1[N:26]([CH3:27])[N:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.[C:35](Cl)(=[O:41])[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>ClCCl>[C:35]([NH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:21])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[CH:7][C:6]=1[C:22]1[N:26]([CH3:27])[N:25]=[CH:24][CH:23]=1)(=[O:41])[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67340Hexanoyl chlorideHCID 46833678N-(4-(2-aminoethoxy)-3-(1-methyl-1H-pyrazol-5-yl)phenyl)-3-methoxybenzamide

Product 1

HCID 57814635HCID 57814635, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-(4-(2-aminoethoxy)-3-(1-methyl-1H-pyrazol-5-yl)phenyl)-3-methoxybenzamide (0.020 g, 0.15 mmol) and triethylamine (0.038 mL, 0.27 mmol) in dichloromethane was added hexanoyl chloride (50 mg, 0.14 mmol), dropwise at room temperature. The mixture was stirred at room temperature overnight. The reaction was quenched with water, extracted with dichloromethane (3×20 mL) and dried over anhydrous MgSO4. The crude product was purified by flash column chromatography. (EtOAc/Hexane=50-90%). N-[4-(2-Hexanoylamino-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-3-methoxy-benzamide was obtained as white solid in 43% yield. LCMS m/z (%)=465 (M+H, 100). 1H NMR (400 MHz, CDCl3) δ ppm 0.9 (t, J=7.1 Hz, 3H), 1.3 (m, 4H), 1.6 (m, 2H), 2.1 (m, 2H), 3.5 (q, J=5.4 Hz, 2H), 3.8 (s, 3H), 3.9 (s, 3H), 4.0 (t, J=5.1 Hz, 2H), 5.5 (m, 1H), 6.3 (d, J=2.0 Hz, 1H), 7.0 (d, J=9.1 Hz, 1H), 7.1 (m, 1H), 7.4 (m, 2H), 7.4 (d, J=2.0 Hz, 1H), 7.6 (d, J=2.0 Hz, 1H), 7.6 (d, J=3.0 Hz, 1H), 7.7 (dd, J=8.8, 2.8 Hz, 1H), 7.8 (s, 1H).

Workup

  1. customdropwise at room temperature
  2. customThe reaction was quenched with water
  3. extractionextracted with dichloromethane (3×20 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-69be5abdd0e247cabbd7042682c71f15
Source dataset
uspto-grants-2016_05
Patent number
US09328107B2

Reaction notes

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