Acetic Acid → HCID 10161526, compound

HRID 2086436Notes

Reaction equation

HRID 2086436 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:10]=[C:9]([CH:11](C)[CH2:12][CH:13]=O)[O:8][N:7]=1.[C:16]1([CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[BH-](OC(C)=O)(OC(C)=O)O[C:37](C)=O.[Na+].C(O)(=O)C>C(Cl)Cl>[C:29]1([CH:22]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:23]2[CH2:24][CH2:25][N:26]([CH2:37][CH2:13][CH2:12][CH2:11][C:9]3[O:8][N:7]=[C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[CH:10]=3)[CH2:27][CH2:28]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 70048BenzhydrylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 22727329HCID 22727329, compound

Product 1

HCID 10161526HCID 10161526, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-(3-(2-thienyl)isoxazol-5-yl)butanal (14 mg, 0.063 mmol) and 1-(diphenylmethyl)piperazine (15.9 mg, 0.063 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (40.1 mg, 0.189 mmol), cold acetic acid (4.4, 0.077 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 17 hr and followed the same processes as in Example 1 to obtain 5.5 mg (19.1%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 17 hr

Sources & evidence

ORD record
ord-003364e3022b428ea2ef8e794b7f307e
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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