Triethylamine → (R)-Benzyl 3-(7-methyl-1H-indazol-5-yl)-1-oxo-1-(pyridin-2-ylmethylamino)propan-2-ylcarbamate

HRID 270745Notes

Reaction equation

HRID 270745 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.[N:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[CH2:42][NH2:43].C([N:46](CC)CC)C.[C:51]([O:54][CH2:55]C)(=[O:53])C>>[CH3:25][C:23]1[CH:24]=[C:16]([CH2:15][C@@H:11]([NH:46][C:51](=[O:53])[O:54][CH2:55][C:27]2[CH:35]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:12](=[O:14])[NH:43][CH2:42][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][N:36]=2)[CH:17]=[C:18]2[C:22]=1[NH:21][N:20]=[CH:19]2

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 8857Ethyl Acetate2×HCID 195092-PyridinemethanamineHCID 666044552-(Benzyloxycarbonyl)-3-(7-methyl-1H-indazol-5-yl)propanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 59833948(R)-Benzyl 3-(7-methyl-1H-indazol-5-yl)-1-oxo-1-(pyridin-2-ylmethylamino)propan-2-ylcarbamate

Conditions

Temperature
40 °C

Procedure

2-(Benzyloxycarbonyl)-3-(7-methyl-1H-indazol-5-yl)propanoic acid (0.47 g, 1.32 mmol), hydroxybenzotriazole (0.2 g, 1.46 mmol), 1-(3-dimethyl aminopropyl)-3-ethyl carbodiimide hydrochloride (0.28 g, 1.46 mmol), and 2-picolyl amine (0.56 mL, 1.46 mmol) were combined in ethyl acetate (10.0 mL). To this solution was added triethylamine (0.56 mL, 4.0 mmol) and the reaction mixture stirred at 40° C. for 2 h. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with 5% citric acid (2×), brine (2×), dried over sodium sulfate, and concentrated to afford 0.42 g (72%).

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 0.42 g (72%)

Sources & evidence

ORD record
ord-63a376cbb96e495b8001dc8257212f8a
Source dataset
uspto-grants-2008_11
Patent number
US07449586B2

Reaction notes

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