Triethylamine → HCID 14500395, compound

HRID 1762826Notes

Reaction equation

HRID 1762826 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[C:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]3[C:22](=[O:23])[C:21]4=[CH:24][S:25][CH:26]=[C:20]4[NH:19][C:18]3=[O:27])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[CH3:35][C:36]([CH3:41])([CH3:40])[C:37](Cl)=[O:38].C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[C:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]3[C:22](=[O:23])[C:21]4=[CH:24][S:25][CH:26]=[C:20]4[N:19]([C:37](=[O:38])[C:36]([CH3:41])([CH3:40])[CH3:35])[C:18]3=[O:27])[CH2:11][CH2:10]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 14500394HCID 14500394, compound

Product 1

HCID 14500395HCID 14500395, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-[2-[4-[bis(4-fluorophenyl)methylene]piperidin-1-yl]ethyl]thieno[3,4-d]pyrimidine-2,4-dione of Example 4 (0.80 g, 1.7 mmol), trimethylacetyl chloride (0.25 ml, 2.0 mmol) and triethylamine (0.84 ml, 6.0 mmol) in methylene chloride (20 ml) was stirred at room temperature for 16 hours. The reaction mixture was washed with water (2×30 ml) and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by flash chromatography on silica gel 60 (80 g) using 1% methanol in methylene chloride as the eluant, to give the title compound (0.35 g, 37% yield) as a colorless solid, mp 69°-72° C. IR(KBr): 1595, 1660 and 1715 cm-1 ; MS (DCI), m/z 564 (MH+); 1H NMR (CDCl3): δ 1.44 (s, 9H), 2.34 (t, J=5 Hz, 4H), 2.61 (t, J=5 Hz, 4H), 2.67 (t, J=7 Hz, 2H), 4.17 (t, J=7 Hz, 2H), 6.58 (d, J=3 Hz, 1H), 6.96-7.08 (m, 8H) and 8.25 (d, J=3 Hz, 1H).

Workup

  1. washThe reaction mixture was washed with water (2×30 ml)
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by flash chromatography on silica gel 60 (80 g)

Sources & evidence

ORD record
ord-b1e436b3bbbe4c03b997934c660f3a5d
Source dataset
uspto-grants-1989_05
Patent number
US04835157

Reaction notes

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