Water → HCID 9912866, compound

HRID 1295484Notes

Reaction equation

HRID 1295484 reaction equation
Cl.[CH2:2]([O:4][C@@H:5]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:11][CH:10]=1)[CH2:6][OH:7])[CH3:3].C(N(CC)CC)C.[F:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1[N:40]=[C:41]=[O:42].O>C(Cl)Cl>[F:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1[NH:40][C:41](=[O:42])[N:17]([CH2:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][C@H:5]([O:4][CH2:2][CH3:3])[CH2:6][OH:7])=[CH:14][CH:13]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5932582,4-Difluorophenyl isocyanateHCID 69434138HCID 69434138, compound

Product 1

HCID 9912866HCID 9912866, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S)-2-Ethoxy-3-{4-[2-(heptylamino)ethyl]phenyl}propan-1-ol hydrochloride (21 mg, 0.059 mmol) and triethyl amine (0.009 ml, 0.065 mmol) were mixed in DCM. 2,4-Di fluorophenyl isocyanate (9.2 mg, 0.059 mmol) was added. The mixture was stirred overnight. Water was added. The organic phase was washed with brine and dried with magnesium sulfate. The solvent was evaporated in vacuum and an oil mixture was left. Chromatography of the oil mixture on a column (ISOLUTE, SI, 200 mg/1 ml) using DCM and MeOH/DCM (1:99) as eluant gave 17 mg desired product, yield 60%.

Workup

  1. washThe organic phase was washed with brine
  2. dry with materialdried with magnesium sulfate
  3. customThe solvent was evaporated in vacuum
  4. waitan oil mixture was left

Sources & evidence

ORD record
ord-335ee020e52147a5a4840f7ab8c87a85
Source dataset
uspto-grants-2007_07
Patent number
US07241923B2

Reaction notes

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