Dichloromethane → HCID 19759054, compound

HRID 1586702Notes

Reaction equation

HRID 1586702 reaction equation
[H-].[Na+].[SH:3][C:4]1[N:9]=[CH:8][CH:7]=[CH:6][N:5]=1.Cl[CH2:11][CH:12]([OH:35])[CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH:20]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:16][CH2:15]1.C(Cl)Cl>CN(C=O)C.CCCCC>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH:20]([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)[N:17]2[CH2:16][CH2:15][N:14]([CH2:13][CH:12]([OH:35])[CH2:11][S:3][C:4]3[N:9]=[CH:8][CH:7]=[CH:6][N:5]=3)[CH2:19][CH2:18]2)=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 103851541-(1-Chloro-2-hydroxy-3-propanyl)-4-(4,4'-difluorobenzhydryl)piperazineHCID 178418793HCID 178418793, compound

Product 1

HCID 19759054HCID 19759054, compoundYield 16.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8003PentaneSolvent

Procedure

To NaH (240 mg, 5 mmol, 50% in oil, prewashed with pentane) in DMF (5 mL) was added 2-mercaptopyrimidine (5 mmol, 560 mg) in portions over 5 minutes at 0° C. After 30 minutes, 1-(1-chloro-2-hydroxy-3-propanyl)-4-(4,4'-diflurobenzhydryl)piperazine (1.9 g, 5 mmol) in DMF (15 mL) was added over 10 minutes under nitrogen. After 12 days, the sodium chloride was removed by filtration and the DMF was removed in vacuo (~0.5 mm Hg, ~50° C.) to give the crude (1.82 g). Flash column chromatography over silica gel using 2% methanol:methylene chloride (2×) and subsequent washings of the product with pentane gave the pure product (380 mg, 16.7%) as a white solid, mp 75°-76° C.; DCI/MS (M+1)=456; (400 MHz) 1H NMR (CDCl3)δ: 8.55 (s, 1H), 8.50 (s, 1H), 7.35 (m, 4H), 7.0 (m, 4H), 4.2 (s, 1H) , 4.0 (m, 1H), 3.3 (m, 2H), 2.65 (m, 2H), 2.4 (m, 8H).

Workup

  1. waitAfter 12 days
  2. customthe sodium chloride was removed by filtration
  3. customthe DMF was removed in vacuo (~0.5 mm Hg, ~50° C.)
  4. customto give the crude (1.82 g)

Sources & evidence

ORD record
ord-8b8a3661d2e9445f9695e8a0869118d2
Source dataset
uspto-grants-1993_06
Patent number
US05215987

Reaction notes

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