Diisopropylethylamine → HCID 25066911, compound

HRID 883333Notes

Reaction equation

[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:17][CH2:18][CH:19]=O)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:21][CH:22]1[CH2:27][NH:26][CH2:25][CH2:24][N:23]1[C:28]1[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:17][CH2:18][CH2:19][N:26]2[CH2:25][CH2:24][N:23]([C:28]3[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=3)[CH:22]([CH3:21])[CH2:27]2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 81531Diisopropylethylamine

HCID 27238042-Methyl-1-(m-tolyl)piperazine

HCID 5049666Sodium triacetoxyborohydride

HCID 866399213-(1-tert-butyl-5-(4-chlorophenyl)-1H-pyrazol-3-yl)propanal

Product 1

HCID 25066911HCID 25066911, compound

Procedure

106 mg (77%) of target compound was obtained by using a method same as in Example 1 by using 3-(1-tert-butyl-5-(4-chlorophenyl)-1H-pyrazol-3-yl)propanal (80 mg, 0.275 mmol), 2-methyl-1-m-tolylpiperazine (52 mg, 0.275 mmol), DIPEA (0.072 mL, 0.413 mmol) and NaBH(OAc)3 (175 mg, 0.825 mmol).

Workup

custom106 mg (77%) of target compound was obtained

Sources & evidence

ORD record: ord-db4087625e2c427e8ff940122a95a1bd
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236806B2

Reaction notes

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