Hydrochloric Acid → HCID 21906016, compound

HRID 2117305Notes

Reaction equation

HRID 2117305 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([N:23]4[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]4)=[O:22])=[CH:17][CH:16]=3)[N:9]=2)=[CH:4][CH:3]=1.[CH:30]([NH2:33])([CH3:32])[CH3:31].C([BH3-])#N.[Na+].Cl>CCO.CCOCC>[ClH:1].[CH3:31][CH:30]([NH:33][CH:26]1[CH2:27][CH2:28][N:23]([C:21]([C:18]2[CH:17]=[CH:16][C:15]([NH:14][C:10]3[N:9]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[CH:13]=[CH:12][N:11]=3)=[CH:20][CH:19]=2)=[O:22])[CH2:24][CH2:25]1)[CH3:32]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6363IsopropylamineHCID 5003444Sodium cyanoborohydrideHCID 21906031HCID 21906031, compound

Product 1

HCID 21906016HCID 21906016, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1-[(4-{[4-(4-chlorophenyl)pyrimidin-2yl]amino}phenyl)carbonyl]piperidin-4-one (400 mg, 0.980 mmol) was dissolved in 10 mL EtOH along with isopropylamine (58 mg, 0.980 mmol). Sodium cyanoborohydride (62 mg, 0.986 mmol) was added and the mixture was stirred at room temperature for 18 hours. The reaction was quenched with water, extracted with ethyl acetate followed by flash chromatography (EtOAc/MeOH; 90:10) to give a residue. This was taken up in ETOH saturated with HCl(g), diluted with ether, filtered to give 4-{[4-(4-chlorophenyl)pyrimidin-2-yl]amino}phenyl 4-[(methylethyl)amino]piperidyl ketone hydrochloride (0.150 g, 30% yield): HPLC Retention time; 6.02 min. (Method B) M+1; 450.4.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. customto give a residue
  4. filtrationfiltered

Sources & evidence

ORD record
ord-adc8c1597cd3451c9bdbbbfcd397532c
Source dataset
uspto-grants-2008_10
Patent number
US07442699B2

Reaction notes

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