Triethylamine → HCID 46235474, compound

HRID 407160Notes

Reaction equation

HRID 407160 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][CH:29]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]([C:24]([OH:26])=O)=[N:20][NH:21]3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)=[O:7].[O:32]1[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][NH2:40])[CH2:34][CH2:33]1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[O:32]1[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][NH:40][C:24]([C:19]2[C:18]3[C:22](=[CH:23][C:15]([C:12]4[CH:11]=[CH:10][C:9]([NH:8][C:6](=[O:7])[C:5]5[CH:27]=[CH:28][CH:29]=[C:3]([C:2]([F:30])([F:1])[F:31])[CH:4]=5)=[CH:14][CH:13]=4)=[CH:16][CH:17]=3)[NH:21][N:20]=2)=[O:26])[CH2:34][CH2:33]1

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 4082852-MorpholinoethylamineHCID 516892Sodium BicarbonateHCID 68621686HCID 68621686, compound

Product 1

HCID 46235474HCID 46235474, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 6-(4-(3-(trifluoromethyl)benzamido)phenyl)-1H-indazole-3-carboxylic acid (6 mg, 14 μmol), morpholinoethyl amine (3 μl, 17 μmol), HOBt (3 mg, 17 μmol), and triethylamine (4 μl, 28 μmol) in N,N-dimethylformamide (0.3 Ml), was added EDCI (4 mg, 21 μmol). After the mixture was stirred at 70° C. for 12 h, the mixture was cooled to room temperature, and ethyl acetate and saturated sodium bicarbonate solution were added. The aqueous layer was extracted with ethyl acetate and the combined organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was triturated in ethyl acetate/hexane to give N-(2-morpholinoethyl)-6-(4-(3-(trifluoromethyl)benzamido)phenyl)-1H-indazole-3-carboxamide (4 mg).

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe combined organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated in ethyl acetate/hexane

Sources & evidence

ORD record
ord-48706420013741bd867b3a6916555443
Source dataset
uspto-grants-2014_06
Patent number
US08754209B2

Reaction notes

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