Dichloromethane → 5-[(6-Methyl-pyrazine-2-carbonyl)-amino]-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester

HRID 1408856Notes

Reaction equation

HRID 1408856 reaction equation
[CH2:1]([O:3][C:4]([C:6]12[CH2:13][C:10]([NH2:14])([CH2:11][CH2:12]1)[CH2:9][CH2:8][CH2:7]2)=[O:5])[CH3:2].C(Cl)Cl.[CH3:18][C:19]1[N:24]=[C:23]([C:25](O)=[O:26])[CH:22]=[N:21][CH:20]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>>[CH2:1]([O:3][C:4]([C:6]12[CH2:13][C:10]([NH:14][C:25]([C:23]3[CH:22]=[N:21][CH:20]=[C:19]([CH3:18])[N:24]=3)=[O:26])([CH2:11][CH2:12]1)[CH2:9][CH2:8][CH2:7]2)=[O:5])[CH3:2]

Participants

6

Reactant 5

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 4708976-Methylpyrazine-2-carboxylic acidHCID 68048103Ethyl 5-aminobicyclo[3.2.1]octane-1-carboxylate

Product 1

HCID 679811065-[(6-Methyl-pyrazine-2-carbonyl)-amino]-bicyclo[3.2.1]octane-1-carboxylic acid ethyl esterYield 75%

Procedure

5-Amino-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester (0.5 g, 2.53 mmol) was dissolved in methylene chloride (10.0 mL, 156 mmol). 6-Methylpyrazine-2-carboxylic acid (0.35 g, 2.53 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.12 g, 2.53 mmol) and triethylamine (0.71 mL, 5.07 mmol) in methylene chloride (10.0 mL, 156 mmol) were added. The mixture was stirred at rt for 2 hours. The mixture was concentrated under reduced pressure. The resulting residue was purified on the CombiFlash® system (hexane/ethyl acetate: 100/0 to 30/70 in 8 min, then hexane/ethyl acetate: 30/70) to afford 0.60 g (75%) of the desired product. ESI-MS m/z: 318 (M+H)+

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified on the CombiFlash® system (hexane/ethyl acetate
  3. wait100/0 to 30/70 in 8 min

Sources & evidence

ORD record
ord-962af31ddd7a40188a4ff1c62422a06c
Source dataset
uspto-grants-2014_12
Patent number
US08921370B2

Reaction notes

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