({[3-(trifluoromethyl)phenyl]sulfonyl}amino)acetic acid → HCID 66787650, compound

HRID 1025761Notes

Reaction equation

HRID 1025761 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([S:9]([NH:12][CH2:13][C:14]([OH:16])=O)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.Cl.Cl.[NH2:21][C@@H:22]1[CH2:26][CH2:25][N:24]([CH:27]2[CH2:32][CH2:31][C:30]([C:34]3[S:35][C:36]([CH2:39][O:40][CH3:41])=[CH:37][N:38]=3)([OH:33])[CH2:29][CH2:28]2)[CH2:23]1>CN(C=O)C>[CH3:41][O:40][CH2:39][C:36]1[S:35][C:34]([C:30]2([OH:33])[CH2:29][CH2:28][CH:27]([N:24]3[CH2:25][CH2:26][C@@H:22]([NH:21][C:14](=[O:16])[CH2:13][NH:12][S:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:18])[F:17])[CH:4]=4)(=[O:10])=[O:11])[CH2:23]3)[CH2:32][CH2:31]2)=[N:38][CH:37]=1

Participants

4

Reactant 2

HCID 697902({[3-(trifluoromethyl)phenyl]sulfonyl}amino)acetic acidHCID 66787114HCID 66787114, compound

Product 1

HCID 66787650HCID 66787650, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ({[3-(trifluoromethyl)phenyl]sulfonyl}amino)acetic acid (64 mg, 0.22 mmol) and 4-[(3R)-3-aminopyrrolidin-1-yl]-1-[5-(methoxymethyl)-1,3-thiazol-2-yl]cyclohexanol dihydrochloride (72 mg, 0.19 mmol) in DMF (5 mL) at 0° C. was added TEA (38 mg, 0.38 mmol) and BOP (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (99 mg, 0.22 mmol). The reaction mixture was stirred for 2 h, and quenched with water (5 mL) and extracted with ethyl acetate (2×25 mL). The organic extracts were combined, washed with saline solution (10 mL), dried over sodium sulfate, concentrated in vacuo. The residue was chromatographed on silica gel, eluting with 1% ammonium hydroxide in ethyl acetate/methanol (100/0 to 90/10). The appropriate fractions were combined to provide two isomers of the desired compound in 1 to 1 ratio with the following characteristics: MS: 577.4 (M+H+, 100%).

Workup

  1. customquenched with water (5 mL)
  2. extractionextracted with ethyl acetate (2×25 mL)
  3. washwashed with saline solution (10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel
  7. washeluting with 1% ammonium hydroxide in ethyl acetate/methanol (100/0 to 90/10)

Sources & evidence

ORD record
ord-c7ee593733a4455d9a6cfd621b29fd8e
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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