Triethylamine → HCID 178461083, compound

HRID 909259Notes

Reaction equation

HRID 909259 reaction equation
Cl.Cl.[NH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]2)=[O:11])[CH2:6][CH2:5]1.[CH2:21]([S:24](Cl)(=[O:26])=[O:25])[CH2:22][CH3:23].CCN(CC)CC>C(Cl)Cl>[CH:18]([N:15]1[CH2:14][CH2:13][N:12]([C:10]([C@H:7]2[CH2:8][CH2:9][C@H:4]([NH:3][S:24]([CH2:21][CH2:22][CH3:23])(=[O:26])=[O:25])[CH2:5][CH2:6]2)=[O:11])[CH2:17][CH2:16]1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 178456373HCID 178456373, compound

Product 1

HCID 178461083HCID 178461083, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 32.6 mg (0.1 mmol) trans-(4-amino-cyclohexyl)-(4-isopropyl-piperazin-1-yl)-methanone, dihydrochloride, 28 mg (0.2 mmol) propane-1-sulfonyl chloride and 101 mg (1 mmol) NEt3 in 2 ml DCM was stirred for 16 h at 40° C. After evaporation methanol and DMF were added and the mixture was subjected to preparative HPLC purification on reversed phase eluting with a gradient of acetonitrile/water (0.1% NEt3). The combined product fractions were evaporated to dryness to yield 13.9 mg (39%) of the title compound. MS (m/e): 360.4 (MH+).

Workup

  1. customAfter evaporation methanol and DMF
  2. additionwere added
  3. customthe mixture was subjected to preparative HPLC purification on reversed phase
  4. washeluting with a gradient of acetonitrile/water (0.1% NEt3)
  5. customThe combined product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-83ce0bb372cc4f278f6ec21fefed9fbf
Source dataset
uspto-grants-2011_09
Patent number
US08017773B2

Reaction notes

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