Triethylamine → HCID 57794671, compound

HRID 2099806Notes

Reaction equation

HRID 2099806 reaction equation
C(OC([CH:11]([CH2:15][C:16]1[CH:17]=[C:18]2[C:22](=[C:23]([CH3:25])[CH:24]=1)[NH:21][N:20]=[CH:19]2)[C:12]([OH:14])=O)=O)C1C=CC=CC=1.O[C:27]1[C:35]2N=NN[C:31]=2[CH:30]=[CH:29][CH:28]=1.[CH3:36][C:37]([CH3:41])([CH3:40])[CH2:38][NH2:39].C([N:44](CC)CC)C.[C:49]([O:52][CH2:53]C)(=[O:51])C>>[CH3:25][C:23]1[CH:24]=[C:16]([CH2:15][CH:11]([NH:44][C:49](=[O:51])[O:52][CH2:53][C:27]2[CH:35]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:12]([NH:39][CH2:38][C:37]([CH3:41])([CH3:40])[CH3:36])=[O:14])[CH:17]=[C:18]2[C:22]=1[NH:21][N:20]=[CH:19]2

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 8857Ethyl Acetate2×HCID 79882NeopentylamineHCID 666044552-(Benzyloxycarbonyl)-3-(7-methyl-1H-indazol-5-yl)propanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 57794671HCID 57794671, compound

Conditions

Temperature
40 °C

Procedure

2-(Benzyloxycarbonyl)-3-(7-methyl-1H-indazol-5-yl)propanoic acid (0.2 g, 0.57 mmol), hydroxybenzotriazole (84 mg, 0.62 mmol), 1-(3-dimethyl aminopropyl)-3-ethyl carbodiimide hydrochloride (0.12 g, 0.62 mmol), and 2,2-dimethylpropan-1-amine (74 μL, 0.62 mmol) were combined in ethyl acetate (6.0 mL). To this solution was added triethylamine (0.24 mL, 1.7 mmol) and the reaction mixture stirred at 40° C. for 2 h. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with 5% citric acid (2×), brine (2×), dried over sodium sulfate, and concentrated to afford 0.21 g (88%). Mass spec.: 423.06 (MH)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with 5% citric acid (2×), brine (2×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto afford 0.21 g (88%)

Sources & evidence

ORD record
ord-4853ddf3a43c45e69641d26035090f92
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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