Ammonia tetrahydrofuran → HCID 178513948, compound

HRID 2176920Notes

Reaction equation

HRID 2176920 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C@@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1.[NH3:17].C1COCC1>S(Cl)(Cl)=O.C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C@@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]([NH2:17])=[O:16])[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 21982362Ammonia tetrahydrofuranHCID 178525751HCID 178525751, compound

Product 1

HCID 178513948HCID 178513948, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

cis-4-(pyridin-2-ylamino)cyclohexanecarboxylic acid (0.22 g, 1.00 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 100 mg of cis-4-(pyridin-2-ylamino)cyclohexanecarboxamide as off 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-ace5718b5692404d8618692482852c9d
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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