Triethylamine → HCID 66588169, compound

HRID 1408213Notes

Reaction equation

HRID 1408213 reaction equation
[F:1][C:2]([F:53])([F:52])[C:3]1[CH:4]=[C:5]([CH:49]=[CH:50][CH:51]=1)[CH2:6][NH:7][C:8]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]2[CH:21]=[C:20]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:19]=[CH:18][C:17]=2[NH:28][C:29](=[O:48])[C:30]2[CH:47]=[CH:46][CH:45]=[C:32]([C:33]([N:35]([CH3:44])[CH2:36][CH2:37][N:38]3[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)=[O:34])[CH:31]=2)[CH:11]=1)=[O:9].[CH2:54]([N:56]([CH2:59]C)CC)[CH3:55].[C:61](Cl)(=O)[O:62]C1C=CC([N+]([O-])=O)=CC=1.C(=O)(O)[O-:75].[Na+]>ClCCl>[CH3:61][O:62][CH2:55][CH2:54][NH:56][C:59]([N:41]1[CH2:40][CH2:39][N:38]([CH2:37][CH2:36][N:35]([CH3:44])[C:33](=[O:34])[C:32]2[CH:45]=[CH:46][CH:47]=[C:30]([C:29]([NH:28][C:17]3[CH:18]=[CH:19][C:20]([N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:21][C:16]=3[C:12]3[CH:11]=[C:10]([C:8](=[O:9])[NH:7][CH2:6][C:5]4[CH:49]=[CH:50][CH:51]=[C:3]([C:2]([F:1])([F:52])[F:53])[CH:4]=4)[CH:15]=[CH:14][N:13]=3)=[O:48])[CH:31]=2)[CH2:43][CH2:42]1)=[O:75]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 66588053HCID 66588053, compound

Product 1

HCID 66588169HCID 66588169, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a 50-mL round-bottom flask, was placed a solution of N1-(2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)-N3-methyl-N3-(2-(piperazin-1-yl)ethyl)isophthalamide (100 mg, 0.14 mmol, 1.00 equiv) in dichloromethane (3 mL), triethylamine (42 mg, 0.42 mmol, 3.00 equiv). This was followed by the addition of 4-nitrophenyl carbonochloridate (31 mg, 0.15 mmol, 1.10 equiv) dropwise with stirring at 0° C. The resulting solution was stirred for 40 min at 25° C. The resulting solution was diluted with 3 mL of sodium bicarbonate. The resulting solution was extracted with 2×5 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 1×5 mL of water and 2×5 mL of Brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 110 mg (90%) of 4-nitrophenyl 4-(2-(N-methyl-3-(4-(piperidin-1-yl)-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)benzamido)ethyl)piperazine-1-carboxylate as a yellow solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. stirringThe resulting solution was stirred for 40 min at 25° C
  3. extractionThe resulting solution was extracted with 2×5 mL of dichloromethane
  4. washThe resulting mixture was washed with 1×5 mL of water and 2×5 mL of Brine
  5. dry with materialThe mixture was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThis resulted in 110 mg (90%) of 4-nitrophenyl 4-(2-(N-methyl-3-(4-(piperidin-1-yl)-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)benzamido)ethyl)piperazine-1-carboxylate as a yellow solid

Sources & evidence

ORD record
ord-9b0f869e50e54d9ca6368d9122231d37
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

Loading…