Acetic Acid → HCID 22347030, compound

HRID 897426Notes

Reaction equation

HRID 897426 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[N:20][C:21]=3[NH2:23])[N:16]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:30]([N:33]1[CH2:38][CH2:37][C:36](=O)[CH2:35][CH2:34]1)([CH3:32])[CH3:31].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>O.ClCCCl>[CH:30]([N:33]1[CH2:38][CH2:37][CH:36]([N:27]2[CH2:28][CH2:29][CH:24]([N:16]3[C:17]4=[N:18][CH:19]=[N:20][C:21]([NH2:23])=[C:22]4[C:14]([C:11]4[CH:10]=[CH:9][C:8]([O:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)=[CH:13][CH:12]=4)=[N:15]3)[CH2:25][CH2:26]2)[CH2:35][CH2:34]1)([CH3:32])[CH3:31]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 793131-(Isopropyl)-4-piperidoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 223472623-(4-phenoxyphenyl)-1-(piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine2×

Product 1

HCID 22347030HCID 22347030, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

3-(4-phenoxyphenyl)-1-(4-piperidinyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Compound 2) (221 mg, 0.572 mmol), 1-isopropyl-4-piperidone(89 mg, 0.63 mmol), sodium triacetoxyborohydride (182 mg, 0.86 mmol) and glacial acetic acid(40 ul, 0.63 mmol) were mixed with 3 ml of 1,2-dichloroethane. After stirring at room temperature overnight, 2 ml of water was added followed by solid sodium bicarbonate until PH reached about 8. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layer was washed, dried and evaporated. The residue was purified by flash column chromatography to give 132 mg of 1-[1-(1-isopropyl-4-piperidinyl)-4-piperidinyl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine. 1H NMR (DMSO) 0.99(d, J=6.54 Hz, 6H), 1.42(m, 2H), 1.72(d, J=11.41 Hz, 2H), 1.88(d, J=9.61 Hz, 2H), 2.14(s, 3H), 2.16(m, 6H), 2.66(m, 2H), 2.83(d,J=10.98 Hz, 2H), 2.98(d,J=8.25 Hz, 2H), 4.62(m, 1H), 7.16(m, 5H), 7.44(m, 2H), 7.67(d, J=8.69 Hz, 2H), 8.23(s, 1H); LC/MS (MH+=512)

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layer was washed
  4. customdried
  5. customevaporated
  6. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-0b771da3a1ab4aa59557ebec75971082
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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