Ethyl Acetate → HCID 68767814, compound

HRID 2279654Notes

Reaction equation

HRID 2279654 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[C:20]1[CH:25]=[CH:24][C:23]([CH:26]([N:29]2[CH2:34][CH2:33]C[CH2:31][CH2:30]2)[CH2:27][NH2:28])=[CH:22][CH:21]=1.F[P-](F)(F)(F)(F)F.[N:42]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:46]2C=CC=CC=2N=N1.CCOC(C)=O>C(#N)C.O>[CH3:46][N:42]1[CH2:31][CH2:30][N:29]([C:26]2([CH2:27][NH:28][C:16]([C:9]3[S:8][C:7]([C:2]4[N:1]=[CH:6][CH:5]=[CH:4][N:3]=4)=[N:11][C:10]=3[C:12]([F:13])([F:14])[F:15])=[O:18])[CH2:22][CH2:21][CH2:20][CH2:25][CH2:24][CH2:23]2)[CH2:34][CH2:33]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 68767814HCID 68767814, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-pyrimidin-2-yl-4-trifluoromethyl-thiazole-5-carboxylic acid (15 mg), 2-(4-chloro-phenyl)-2-piperidin-1-yl-ethylamine (15 mg), BOP (25 mg) and TEA (10 mg) in ACN (1 mL) is stirred at RT overnight. EtOAc and water are 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)=483.21; RT=1.15 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-421db6fc1fcd495bbe958a29776bd390
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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