Pyridine → HCID 178484222, compound

HRID 2409815Notes

Reaction equation

HRID 2409815 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:22][C:3]=1[C:4]([NH:6][C:7]1[NH:8][N:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:11]=1)=[O:5].N1C=CC=CC=1.[CH3:38][N:39]([CH2:51][CH2:52][N:53]1[CH2:58][CH2:57][O:56][CH2:55][CH2:54]1)[C:40]([C:42]1[CH:43]=[C:44]([CH:48]=[CH:49][CH:50]=1)[C:45](Cl)=[O:46])=[O:41]>ClCCl.C(OCC)(=O)C>[CH3:38][N:39]([CH2:51][CH2:52][N:53]1[CH2:58][CH2:57][O:56][CH2:55][CH2:54]1)[C:40](=[O:41])[C:42]1[CH:50]=[CH:49][CH:48]=[C:44]([C:45]([NH:1][C:2]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:22][C:3]=2[C:4](=[O:5])[NH:6][C:7]2[NH:8][N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=3)[N:11]=2)=[O:46])[CH:43]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 867052033-(Methyl(2-morpholinoethyl)carbamoyl)benzoyl chlorideHCID 178507694HCID 178507694, compound

Product 1

HCID 178484222HCID 178484222, compoundYield 14.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-5-(piperidin-1-yl)-N-(5-(3-(trifluoromethyl)phenyl)-2H-1,2,4-triazol-3-yl)benzamide (50 mg, 0.12 mmol, 1.00 equiv) in dichloromethane (3 mL) was added pyridine (73 mg, 0.92 mmol, 8.00 equiv) followed by the dropwise addition of a solution of 3-(methyl(2-morpholinoethyl)carbamoyl)benzoyl chloride (54 mg, 0.17 mmol, 1.50 equiv) in dichloromethane (2 mL) and the resulting solution was stirred for 30 min at room temperature. The mixture was diluted with 50 mL of ethyl acetate, washed with 2×20 mL of NH4Cl and 2×20 mL of brine, dried over anhydrous sodium sulfate and then concentrated under vacuum. The crude product (50 mg) was purified by reverse phase HPLC eluting with a water/CH3CN gradient containing 0.05% TFA. The product was obtained as 12 mg (10%) of a yellow solid. 1H-NMR (300 MHz, CD3OD, ppm): δ 8.34 (m, 3H), 8.17 (t, J=7.8 Hz, 2H), 7.73 (m, 5H), 7.42 (m, 1H), 3.98 (s, 2H), 3.55 (m, 3H), 3.40 (m, 5H), 3.29 (m, 1H), 3.09 (m, 3H), 1.86 (d, J=4.8 Hz, 4H), 1.71 (t, J=5.1 Hz, 2H). MS (ES, m/z): 705 [M+H]+.

Workup

  1. washwashed with 2×20 mL of NH4Cl and 2×20 mL of brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe crude product (50 mg) was purified by reverse phase HPLC
  5. washeluting with a water/CH3CN gradient
  6. additioncontaining 0.05% TFA

Sources & evidence

ORD record
ord-44c9f3b453d14e83af9bd1130cf22931
Source dataset
uspto-grants-2014_08
Patent number
US08815910B2

Reaction notes

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