Phenethylamine → HCID 66995132, compound

HRID 1668412Notes

Reaction equation

HRID 1668412 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([OH:16])=O)[N:9]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:27](C(C)C)CC)(C)C.[CH2:33](N)[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@:10]([C:14](=[O:16])[NH2:27])([CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:9]1[C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

8

Reactant 5

HCID 1001PhenethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10871237PYR412

Product 1

HCID 66995132HCID 66995132, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (S)-tetrahydro-pyridazine-1,2,3-tricarboxylic acid 1,2-di-tert-butyl ester (83 mg, 2.5 mmol) in DMF (10 mL) at room temperature, is added diisopropylethylamine (1.4 mL) slowly. After stirring at room temperature for 20 minutes, to the reaction mixture, is added phenethylamine (445 mg, 3.67 mmol), and followed by a solution of HOBT (545 mg, 4.04 mmol) and HBTU (1.53 g, 4.04 mmol) in DMF (10 mL). After stirring for 1.5 hours at room temperature, the reaction solution is diluted with ether (100 mL), and washed with water (2×50 mL). The combined organic solution is concentrated. The crude product is diluted with CH2Cl2 and dried over Na2SO4, and purified by chromatography (CH2Cl2/MeOH:97/3) to give (S)-3-phenethyl carbamoyl-tetrahydro-pyridazine-1,2-dicarboxylic acid di-tert-butyl ester as pale gum (920 mg, 83.6% in two steps). (NMR and MS data confirmed, U-3133-57-26).

Workup

  1. stirringAfter stirring for 1.5 hours at room temperature
  2. washwashed with water (2×50 mL)
  3. concentrationThe combined organic solution is concentrated
  4. additionThe crude product is diluted with CH2Cl2
  5. dry with materialdried over Na2SO4
  6. custompurified by chromatography (CH2Cl2/MeOH:97/3)

Sources & evidence

ORD record
ord-047b29c09beb40938fae80d977431bca
Source dataset
uspto-grants-2011_08
Patent number
US07989441B2

Reaction notes

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