Trifluoroacetic acid → HCID 59164595, compound

HRID 1441692Notes

Reaction equation

HRID 1441692 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]([CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[C:34]([CH3:40])[CH:33]=2)[C:17]2[S:18][C:19]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:20]=3[N:21]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.NCCC1C=CC(C#N)=C(C)C=1.CC(OC(N1CCC(CC=O)CC1)=O)(C)C.ClC1SC2C=C(C(F)(F)F)C=CC=2N=1.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[CH3:40][C:34]1[CH:33]=[C:32]([CH2:31][CH2:30][N:16]([CH2:15][CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[C:17]2[S:18][C:19]3[CH:25]=[C:24]([C:26]([F:28])([F:27])[F:29])[CH:23]=[CH:22][C:20]=3[N:21]=2)[CH:37]=[CH:36][C:35]=1[C:38]#[N:39]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 10353694tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylateHCID 114704192-Chloro-6-trifluoromethylbenzothiazoleHCID 59164596HCID 59164596, compoundHCID 68406062HCID 68406062, compound

Product 1

HCID 59164595HCID 59164595, compoundYield 35.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.1 g 4-{2-[[2-(4-Cyano-3-methyl-phenyl)-ethyl]-(6-trifluoromethyl-benzothiazol-2-yl)-amino]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester [prepared according to the method described in Example 1 and 5 from 4-(2-Amino-ethyl)-2-methyl-benzonitrile trifluoro acetate, N-boc-piperidinyl-4-acetaldehyde and 2-Chloro-6-trifluoromethyl-benzothiazole] were dissolved in 50 ml dichloromethane. 5 ml trifluoroacetic acid were added and the reaction mixture was stirred at room temperature for one hour. 150 ml ethyl acetate were added and the mixture was washed three times with saturated NaHCO3 solution. The organic layer was dried over MgSO4 and then the solvent was removed in vacuo. The residue was purified by RP-HPLC to obtain 325 mg 2-Methyl-4-{2-[(2-piperidin-4-yl-ethyl)-(6-trifluoromethyl-benzothiazol-2-yl)-amino]-ethyl}-benzonitrile.

Workup

  1. washthe mixture was washed three times with saturated NaHCO3 solution
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-d22327a4dd2e4452884e5e6bcbc1c048
Source dataset
uspto-grants-2010_02
Patent number
US07655679B2

Reaction notes

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