Hydrochloric Acid → HCID 178502708, compound

HRID 25670Notes

Reaction equation

HRID 25670 reaction equation
[CH3:1][N:2]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C@H:3]1[CH2:8][CH2:7][C@H:6]([O:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)[CH2:5][CH2:4]1.C[N:30]1[CH2:35]COCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH3:58][O:59]CN.OS([O-])(=O)=O.[K+]>C(Cl)Cl>[CH3:58][O:59][N:30]([CH3:35])[C:13](=[O:15])[CH2:12][CH2:11][CH2:10][O:9][C@H:6]1[CH2:7][CH2:8][C@H:3]([N:2]([CH3:1])[S:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:4][CH2:5]1

Participants

9

Reactant 7

HCID 313Hydrochloric Acid2×HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516920Potassium bisulfateHCID 177781771-MethoxymethanamineHCID 178484854HCID 178484854, compound

Product 1

HCID 178502708HCID 178502708, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

250 mg (0.59 mmol) trans-4-{4-[Methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-butyric acid in 7 ml CH2Cl2 were treated with 0.33 ml (2.95 mmol) NMM, 18 mg (0.12 mmol, 0.2 eq) HOBT, 147 mg (0.77 mmol, 1.3 eq) EDCI.hydrochloride and 127 mg (1.3 mmol, 2.2 eq) N-Methoxymethylamine.hydro-chloride. The mixture was stirred at RT for 3 h, was acidified by adding 1M KHSO4 and extracted with CH2Cl2. The combined organic phases were washed with brine, dried over Na2SO4 and evaporated to yield 260 mg (94%) trans-N-Methoxy-N-methyl-4-{4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-butyramide as light yellow oil, MS: 467 (MH+).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-ecebf2d422eb4eb7adba2f35ed9042fc
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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