N-Methylpropylamine → HCID 178457210, compound

HRID 25649Notes

Reaction equation

HRID 25649 reaction equation
I[CH2:2][CH2:3][CH2:4][C:5]#[C:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]([CH3:27])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:9][CH2:8]1.[CH3:28][NH:29][CH2:30][CH2:31][CH3:32]>CO>[CH3:27][N:13]([C@H:10]1[CH2:11][CH2:12][C@H:7]([C:6]#[C:5][CH2:4][CH2:3][CH2:2][N:29]([CH3:28])[CH2:30][CH2:31][CH3:32])[CH2:8][CH2:9]1)[S:14]([C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 12315N-MethylpropylamineHCID 178484794HCID 178484794, compound

Product 1

HCID 178457210HCID 178457210, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

320 mg (corresponds to 0.59 mmol) of crude trans-N-[4-(5-Iodo-pent-1-ynyl)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide in 6 ml MeOH was treated with 0.6 ml (5.93 mmol) of N-methylpropylamine. The reaction was stirred overnight at 65° C. and partitioned between aqueous 1N NaOH /Et2O (3×), the organic phases were dried over Na2SO4 and evaporated. Purification by flash column chromatography on silica gel (CH2Cl2, then CH2Cl2/MeOH 95:5 to 9:1) gave 128 mg (47% over two steps) of trans-N-Methyl-N-{4-[5-(methyl-propyl-amino)-pent-1-ynyl]-cyclohexyl}-4-trifluoromethyl-benzenesulfonamide, MS: 459 (MH+). The following compounds can be obtained in analogy:

Workup

  1. custompartitioned between aqueous 1N NaOH /Et2O (3×)
  2. dry with materialthe organic phases were dried over Na2SO4
  3. customevaporated
  4. customPurification by flash column chromatography on silica gel (CH2Cl2

Sources & evidence

ORD record
ord-5e62d54e190a458e8ae513f47a3c8f7b
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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