Acetic Acid → HCID 16221920, compound

HRID 1678492Notes

Reaction equation

HRID 1678492 reaction equation
[O:1]=[S:2]1(=[O:33])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[C:28]([CH:30]=O)[CH:27]=[CH:26][C:25]=4[CH3:32])=[CH:20][CH:19]=3)=[O:17])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[Br:34][C:35]1[CH:36]=[C:37]([CH:39]=[CH:40][CH:41]=1)[NH2:38].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[O:33]=[S:2]1(=[O:1])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:16]([C:18]3[CH:19]=[CH:20][C:21]([C:24]4[CH:29]=[C:28]([CH2:30][NH:38][C:37]5[CH:39]=[CH:40][CH:41]=[C:35]([Br:34])[CH:36]=5)[CH:27]=[CH:26][C:25]=4[CH3:32])=[CH:22][CH:23]=3)=[O:17])=[CH:13][CH:14]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 115623-BromoanilineHCID 5049666Sodium triacetoxyborohydrideHCID 59822333HCID 59822333, compound

Product 1

HCID 16221920HCID 16221920, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5′-Formyl-2′-methyl-biphenyl-4-carboxylic acid [4-(1,1-dioxo-1lambda*6*-thiomorpholin-4-ylmethyl)-phenyl]-amide (40 mg) and 3-bromo-aniline (18 mg) were stirred together in dry dichloromethane (10 ml) containing 3 A molecular sieves. The mixture was then heated to 40 C for 4 h. Sodium (triacetoxy)borohydride (50 mg) and glacial acetic acid (1 ml) were then added and stirring continued at 20 C for 18 h. The sieves were then removed by filtration and the mother liquor evaporated. The residue was purified on silica gel. Elution with dichloromethane:ethanol:0.880 ammonia; 200:8:1 gave the title compound as a pale yellow solid (32 mg).

Workup

  1. additioncontaining 3 A molecular sieves
  2. temperatureThe mixture was then heated to 40 C for 4 h
  3. customThe sieves were then removed by filtration
  4. customthe mother liquor evaporated
  5. customThe residue was purified on silica gel
  6. washElution with dichloromethane

Sources & evidence

ORD record
ord-e0fa66f1866e41269447cc2f22ddc902
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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