Triethylamine → HCID 68433051, compound

HRID 1867436Notes

Reaction equation

HRID 1867436 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[N:16]([CH2:21][CH:22]3[CH2:24][O:23]3)[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[F:26][CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.CCN(CC)CC>CO>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[N:16]([CH2:21][CH:22]([OH:23])[CH2:24][N:30]3[CH2:31][CH2:32][CH:27]([F:26])[CH2:28][CH2:29]3)[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27591584-Fluoropiperidine hydrochlorideHCID 87453574HCID 87453574, compound

Product 1

HCID 68433051HCID 68433051, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 0.080 g (0.22 mmol) of (rac)-1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-4-oxiranylmethyl-[1,4]diazepan-5-one (example 166A) in 0.5 ml of MeOH was treated with 0.038 (0.26 mmol) of 4-fluoropiperidine hydrochloride and 0.15 ml (1.08 mmol) of Et3N in 0.5 ml of MeOH. The reaction was stirred for 24 h at RT, partitioned between aqueous saturated NaHCO3 and extracted with Et2O (3×). The organic phase was dried over Na2SO4 and evaporated to give after flash silica gel column (CH2Cl2/MeOH 98:2) 0.0099 g (10%) of the title compound as white foam. MS: 471.9 (MH+, 2Cl).

Workup

  1. custompartitioned between aqueous saturated NaHCO3
  2. extractionextracted with Et2O (3×)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-33f8bcd82f1a45b5afffc3a63f3928c1
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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