Dimethylamine → 1-(4-methoxyphenyl)-6-[4-(2-oxo-1-piperidinyl)phenyl]1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one

HRID 1064044Notes

Reaction equation

HRID 1064044 reaction equation
Br[C:2]1[C:10]2[CH2:9][CH2:8][N:7]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:22][CH2:21][CH2:20][CH2:19][C:18]4=[O:23])=[CH:13][CH:12]=3)[C:6](=[O:24])[C:5]=2[N:4]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[N:3]=1.CNC.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1>C1(C)C=CC=CC=1.O1CCOCC1>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([N:4]2[C:5]3[C:6](=[O:24])[N:7]([C:11]4[CH:16]=[CH:15][C:14]([N:17]5[CH2:22][CH2:21][CH2:20][CH2:19][C:18]5=[O:23])=[CH:13][CH:12]=4)[CH2:8][CH2:9][C:10]=3[CH:2]=[N:3]2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 101175123-bromo-1-(4-methoxyphenyl)-6-[4-(2-oxo-1-piperidinyl)phenyl]1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-oneHCID 23676156Sodium t-butoxide

Product 1

HCID 102733951-(4-methoxyphenyl)-6-[4-(2-oxo-1-piperidinyl)phenyl]1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-oneYield 20%

Reagents, catalysts & solvents 1

HCID 21840791Dioxane tolueneSolvent

Conditions

Temperature
85 °C

Procedure

To 3-bromo-1-(4-methoxyphenyl)-6-[4-(2-oxo-1-piperidinyl)phenyl]1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one (Example 21)(0.15 g, 0.3 mmol), dimethylamine (2M THF, 1.5 mL, 3 mmol), sodium t-butoxide (88 mg, 0.9 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (7 mg), was added toluene/dioxane (1:1) (15 mL) and the mixture was degassed with N2. Pd2(dba)3 was added and the reaction was heated to 85° C. for 24 h. The reaction was cooled, diluted with ethyl acetate and filtered through Celite®. Purification by HPLC and freeze-drying afforded 25 mg (18%) of the title compound; HRMS (M+Na)+ for C24H24NaN4O3 was 439.1726; 1H NMR (CDCl3) δ 7.59 (s, 1H), 7.47 (d, j=8.8 Hz, 2H), 7.36 (d, j=8.8 Hz, 2H), 7.26 (d, j=9.1 Hz, 2H), 6.92 (d, j=9.2 Hz, 2H), 4.10 (t, j=6.6 Hz, 2H), 3.60 (m, 2H), 3.81 (s, 3H), 3.03 (t, j=6.6 Hz, 2H), 2.57 (m, 2H), 1.94 (m, 4H) ppm.

Workup

  1. customthe mixture was degassed with N2
  2. additionPd2(dba)3 was added
  3. temperatureThe reaction was cooled
  4. additiondiluted with ethyl acetate
  5. filtrationfiltered through Celite®
  6. customPurification by HPLC
  7. customfreeze-drying

Sources & evidence

ORD record
ord-50bc2eae846141ddac9a837ad6d3229f
Source dataset
uspto-grants-2005_11
Patent number
US06967208B2

Reaction notes

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