Ammonia tetrahydrofuran → HCID 178513953, compound

HRID 2176937Notes

Reaction equation

HRID 2176937 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]1.[NH3:16].C1COCC1>S(Cl)(Cl)=O.CO.C(Cl)Cl>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([NH2:16])=[O:15])[CH2:9][CH2:8]1

Participants

6

Reactant 2

HCID 21982362Ammonia tetrahydrofuranHCID 178525766HCID 178525766, compound

Product 1

HCID 178513953HCID 178513953, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of cis-4-(thiazol-2-ylamino)cyclohexanecarboxylic acid (200 mg, 0.88 mmol) in thionyl chloride (1 ml) was stirred for 1 h at room temperature. The excess thionyl chloride was removed in vacuo to give the crude acid chloride. Liquid ammonia/THF (1:1, 15 ml) was added to the above prepared acid chloride solution at −60° C. and allowed to warm up to room temperature. The reaction mixture was diluted with 10% MeOH in DCM and filtered. The filtrate was concentrated under reduced pressure to afford 140 mg (70%) of cis-4-(thiazol-2-ylamino)cyclohexanecarboxamide as white solid.

Workup

  1. customThe excess thionyl chloride was removed in vacuo
  2. customto give the crude acid chloride
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2b0428cd59204f6ca053515e2d19ac93
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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