1,2-Dichloroethane → phenylmethyl [(1S)-2,2-dimethyl-1-({(1S,4S)-5-[(5-phenyl-2-pyridinyl)carbonyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)propyl]carbamate

HRID 2098464Notes

Reaction equation

HRID 2098464 reaction equation
[C@H:1]12[CH2:7][C@H:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]([C@@H:10]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[C:26]1([C:32]2[CH:33]=[CH:34][C:35]([C:38](O)=[O:39])=[N:36][CH:37]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.O>[CH3:13][C:11]([CH3:12])([CH3:14])[C@H:10]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:8]([N:2]1[CH2:3][C@@H:4]2[CH2:7][C@H:1]1[CH2:6][N:5]2[C:38]([C:35]1[CH:34]=[CH:33][C:32]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:37][N:36]=1)=[O:39])=[O:9]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27628705-phenylpyridine-2-carboxylic AcidHCID 70232205phenylmethyl {(1S)-1-[(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-ylcarbonyl]-2,2-dimethylpropyl}carbamate

Product 1

HCID 68315921phenylmethyl [(1S)-2,2-dimethyl-1-({(1S,4S)-5-[(5-phenyl-2-pyridinyl)carbonyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)propyl]carbamateYield 103.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of phenylmethyl {(1S)-1-[(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-ylcarbonyl]-2,2-dimethylpropyl}carbamate (826 mg, 2.39 mmol), 5-phenyl-2-pyridinecarboxylic acid (500 mg, 2.5 mmol), EDC (550 mg, 2.87 mmol), HOBt (65 mg, 0.48 mmol), NMM (736 mg, 7.17 mmol) in CH2Cl2 (10 mL) was stirred at room temperature for 18 h. The reaction was diluted with water and CH2Cl2. The two layers were separated; the organic dried over anhydrous Na2SO4 and concentrated to give the title compound (1.3 g) as a pale brown oil. LCMS (m/z): 527.3 (M+H).

Workup

  1. customThe two layers were separated
  2. dry with materialthe organic dried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1d69b6e9183047d380c8a7a417ca2487
Source dataset
uspto-grants-2013_05
Patent number
US08450484B2

Reaction notes

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