Benzhydrylamine → HCID 86680446, compound

HRID 240435Notes

Reaction equation

HRID 240435 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[CH2:14][C@@H:15]([C:17]([OH:19])=O)[CH2:16][C@H:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N=C=NCCCN(C)C)C.O.OC1C2N=NNC=2C=CC=1.[C:42]1([CH:48]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[NH2:49])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>ClCCl.O>[CH:48]([NH:49][C:17]([C@@H:15]1[CH2:14][N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][C@@H:10]2[CH2:16]1)=[O:19])([C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

7

Reactant 4

HCID 7036BenzhydrylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 86680447Pyrrolo[1,2-a]pyrazine-2,7(1H)-dicarboxylic acid, hexahydro-, 2-(1,1-dimethylethyl) ester, (7S,8aS)-HCID 178526939HCID 178526939, compound

Product 1

HCID 86680446HCID 86680446, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (7S,8aS)-2-(tert-butoxycarbonyl)octahydropyrrolo[1,2-a]pyrazine-7-carboxylic acid (80 mg, 0.296 mmol) in dichloromethane (2 mL) was added a solution of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (68.9 mg, 0.444 mmol) and hydroxybenzotriazole hydrate (40.0 mg, 0.296 mmol) in dichloromethane (1 mL). The mixture was stirred at room temperature for 1 hour, and then diphenylmethanamine (54.2 mg, 0.296 mmol) was added. After stirring for three days the mixture was poured into water (10 mL). The mixture was extracted with dichloromethane (3×5 mL). The organic fractions were concentrated, and the residue was purified by flash chromatography (dichloromethane/methanol=25:1) to give the title compound. MS (ESI) m/z 436 (M+H)+.

Workup

  1. stirringAfter stirring for three days the mixture
  2. extractionThe mixture was extracted with dichloromethane (3×5 mL)
  3. concentrationThe organic fractions were concentrated
  4. customthe residue was purified by flash chromatography (dichloromethane/methanol=25:1)

Sources & evidence

ORD record
ord-b674d5ba628842d59de13675bc6726d0
Source dataset
uspto-grants-2014_02
Patent number
US08648074B2

Reaction notes

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