Diisopropylethylamine → HCID 10179841, compound

HRID 1838287Notes

Reaction equation

HRID 1838287 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH2:15][CH:14]([CH2:16][CH2:17][CH:18]=O)[O:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.Cl.[N:22]1[CH:27]=[CH:26][CH:25]=[N:24][C:23]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH2:15][CH:14]([CH2:16][CH2:17][CH2:18][N:31]3[CH2:32][CH2:33][N:28]([C:23]4[N:22]=[CH:27][CH:26]=[CH:25][N:24]=4)[CH2:29][CH2:30]3)[O:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 116802722-Piperazinylpyrimidine dihydrochlorideHCID 187533883-[3-(3,4-Dimethoxyphenyl)-4,5-dihydroisoxazol-5-yl]propanal

Product 1

HCID 10179841HCID 10179841, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[3-(3,4-Dimethoxyphenyl)-4,5-dihydroisoxazol-5-yl]propanal (24.9 mg, 0.092 mmol), 1-(2-pyrimidyl)piperazine dihydrochloride (20.0 mg, 0.084 mmol), molecular sieve (5 beads), NaBH(OAc)3 (53.6 mg, 0.252 mmol) and diisopropylethylamine (53.9 L, 0.168 mmol) were reacted in 3 mL of methylene chloride for about 12 hr. With the following processes the same as in Example 1, 23.6 mg (68.2%) of the target compound was obtained.

Sources & evidence

ORD record
ord-130b8d5811da4f8891b21919bfdf470d
Source dataset
uspto-grants-2004_01
Patent number
US06673800B2

Reaction notes

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