Ammonia tetrahydrofuran → HCID 178513951, compound

HRID 1896293Notes

Reaction equation

HRID 1896293 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C@@H:8]2[CH2:13][CH2:12][C@H:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]2)=[CH:3][CH:2]=1.[NH3:17].C1COCC1>S(Cl)(Cl)=O.C(Cl)Cl>[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C@@H:8]2[CH2:13][CH2:12][C@H:11]([C:14]([NH2:17])=[O:16])[CH2:10][CH2:9]2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 21982362Ammonia tetrahydrofuranHCID 178525756HCID 178525756, compound

Product 1

HCID 178513951HCID 178513951, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

cis-4-(Pyridin-4-ylamino)cyclohexanecarboxylic acid (600 mg, 2.74 mmol) was dissolved in thionyl chloride (2 ml) at room temperature and stirred for 1 h. The reaction mixture was concentrated under reduced pressure to yield the crude acid chloride, which was added to liquid ammonia/THF (1:1, 15 ml) and allowed to stir at room temperature. The reaction mixture was diluted with DCM and filtered. The filtrate was concentrated under reduced pressure to afford 400 mg (68%) of cis-4-(pyridin-4-ylamino)cyclohexanecarboxamide as white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto yield the crude acid chloride, which
  3. stirringto stir at room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-608d3bae804b4fb789e708808a2f1194
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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