Triethylamine → HCID 67437196, compound

HRID 1968882Notes

Reaction equation

HRID 1968882 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=O)[CH:5]=[CH:4][CH:3]=1.[C:14]([O:18][C:19](=[O:35])[NH:20][C@H:21]([CH2:26][NH:27][C:28]1[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][CH:29]=1)[C@@H:22]([CH3:25])[CH2:23][CH3:24])([CH3:17])([CH3:16])[CH3:15].C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[C:14]([O:18][C:19](=[O:35])[NH:20][C@H:21]([CH2:26][N:27]([C:28]1[CH:29]=[CH:30][C:31]([Br:34])=[CH:32][CH:33]=1)[C:11]([C@@H:9]1[CH2:10][C@H:8]1[C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=1)=[O:13])[C@@H:22]([CH3:25])[CH2:23][CH3:24])([CH3:16])([CH3:17])[CH3:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 67114406HCID 67114406, compoundHCID 67436431HCID 67436431, compound

Product 1

HCID 67437196HCID 67437196, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of trans-2-(6-fluoro-pyridin-2-yl)-cyclopropanecarboxylic acid (120 mg, 0.55 mmol) in thionyl chloride (2 mL) was heated at reflux for over night. The mixture was concentrated and dried under high vacuum for 3 h. Then the residue was dissolved in DCM (3 mL) and added dropwise to a solution of {(1S,2S)1-[(4-Bromo-phenylamino)-methyl]-2-methyl-butyl}-carbamic acid tert-butyl ester (205 mg, 0.55 mmol) and triethyl amine (153 uL, 1.1 mmol) in DCM (3 mL). The resulting mixture was stirred at rt for overnight. The reaction mixture was concentrated and the residue was subjected to ISCO (12 g column, 0-40% EtOAc in hexane over 25 min.) to give the desired product (235 mg, 80%). MS (MH+ 534 and 536).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for over night
  3. concentrationThe mixture was concentrated
  4. customdried under high vacuum for 3 h
  5. dissolutionThen the residue was dissolved in DCM (3 mL)
  6. concentrationThe reaction mixture was concentrated
  7. customwas subjected to ISCO (12 g column, 0-40% EtOAc in hexane over 25 min.)

Sources & evidence

ORD record
ord-6b0204a809594c85ad2af734bdd7646e
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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