Triethylamine → HCID 67114202, compound

HRID 1968871Notes

Reaction equation

HRID 1968871 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:21]1([CH2:26][NH:27][C:28]2[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][CH:29]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1)([CH3:17])([CH3:16])[CH3:15].C(N(CC)CC)C.CCOC(C)=O>S(Cl)(Cl)=O.C(Cl)Cl.CCCCCC>[C:14]([O:18][C:19](=[O:35])[NH:20][C:21]1([CH2:26][N:27]([C:28]2[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][CH:29]=2)[C:11]([C@@H:9]2[CH2:10][C@H:8]2[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=2)=[O:13])[CH2:22][CH2:23][CH2:24][CH2:25]1)([CH3:17])([CH3:15])[CH3:16]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 67114178HCID 67114178, compoundHCID 67114406HCID 67114406, compound

Product 1

HCID 67114202HCID 67114202, compoundYield 72.6%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of trans-2-(6-fluoro-pyridin-2yl)-cyclopropanecarboxylic acid (˜0.9 mmol) in thionyl chloride (2 mL) was heated at reflux for overnight. The mixture was concentrated and dried under high vacuum for 2 h. Then the residue was dissolved in DCM (4 mL) and added dropwise to a solution of {1-[(4-Bromo-phenylamino)-methyl]-cyclopentyl}-carbamic acid tert-butyl ester (370 mg, 1 mmol) and triethyl amine (280 uL) in DCM (4 mL). The resulting mixture was stirred at rt for over night. The reaction mixture was subjected to flash column directly (20% EtOAc in hexane) to give the desired product as a white solid (348 mg, ˜70%). MS (MH+ 532 and 534).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for overnight
  3. concentrationThe mixture was concentrated
  4. customdried under high vacuum for 2 h
  5. dissolutionThen the residue was dissolved in DCM (4 mL)

Sources & evidence

ORD record
ord-d139b07ebf08423cbe28498f55ad7090
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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