Triethylamine → N-[4-(1,1-Dioxo-1lambda6-thiomorpholin-4-yl)-phenyl]-2-oxo-2-(2-phenyl-indolizin-3-yl)-acetamide

HRID 1910838Notes

Reaction equation

HRID 1910838 reaction equation
[O:1]=[C:2]([C:6]1[N:14]2[C:9]([CH:10]=[CH:11][CH:12]=[CH:13]2)=[CH:8][C:7]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3](Cl)=[O:4].[O:21]=[S:22]1(=[O:35])[CH2:27][CH2:26][N:25]([C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)[CH2:24][CH2:23]1.C(N(CC)CC)C>C1COCC1>[O:35]=[S:22]1(=[O:21])[CH2:23][CH2:24][N:25]([C:28]2[CH:29]=[CH:30][C:31]([NH:34][C:3](=[O:4])[C:2](=[O:1])[C:6]3[N:14]4[C:9]([CH:10]=[CH:11][CH:12]=[CH:13]4)=[CH:8][C:7]=3[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:32][CH:33]=2)[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 50082602-oxo-2-(2-phenylindolizin-3-yl)acetyl ChlorideHCID 263703844-(4-Aminophenyl)thiomorpholine 1,1-Dioxide

Product 1

HCID 24999469N-[4-(1,1-Dioxo-1lambda6-thiomorpholin-4-yl)-phenyl]-2-oxo-2-(2-phenyl-indolizin-3-yl)-acetamideYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of oxo-(2-phenyl-indolizin-3-yl)-acetyl chloride (0.12 g, 0.42 mmol) in THF was added to a solution of 4-(1,1-dioxo-1λ6-thiomorpholin-4-yl)-phenylamine (70 mg, 0.31 mmol) and triethylamine (85 mg, 0.85 mmol) in THF (10 mL) at 0° C., then the mixture was stirred for 8 h at r.t. The mixture was concentrated to dryness and washed with water to give a crude product which was triturated with methanol to afford the title compound (70 mg, 48%) as a solid.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. washwashed with water
  3. customto give a crude product which
  4. customwas triturated with methanol

Sources & evidence

ORD record
ord-44379e4d4b8d4907b1c3c3a6bb595743
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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