Ethyl Acetate → HCID 68768652, compound

HRID 2279653Notes

Reaction equation

HRID 2279653 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[S:8][C:9]([C:16]([OH:18])=O)=[C:10]([C:12]([F:15])([F:14])[F:13])[N:11]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:27][NH2:28])=[CH:22][CH:21]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCOC(C)=O>C(#N)C.O>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([N:29]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]2)[CH2:27][NH:28][C:16]([C:9]2[S:8][C:7]([C:2]3[N:1]=[CH:6][CH:5]=[CH:4][N:3]=3)=[N:11][C:10]=2[C:12]([F:13])([F:14])[F:15])=[O:18])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 166424352-(4-Chlorophenyl)-2-(piperidin-1-yl)ethan-1-amineHCID 59580006HCID 59580006, compound

Product 1

HCID 68768652HCID 68768652, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-pyrimidin-2-yl-4-trifluoromethyl-thiazole-5-carboxylic acid (60 mg), 2-(4-chloro-phenyl)-2-piperidin-1-yl-ethylamine (60 mg), BOP (100 mg) and TEA (40 mg) in ACN (1 mL) is stirred at RT overnight. EtOAc and water added to the mixture and the organic layer is separated, washed twice with water and concentrated in vacuo. The residue is purified by PTLC (10% MeOH in methylene chloride) to give the title compound. MS (M+1)=496.09; RT=1.14 min. *IC50.

Workup

  1. customthe organic layer is separated
  2. washwashed twice with water
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by PTLC (10% MeOH in methylene chloride)

Sources & evidence

ORD record
ord-86ef3cdced1e47be85d00bb3b1f4b22c
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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