Acetone → HCID 46831268, compound

HRID 2368772Notes

Reaction equation

HRID 2368772 reaction equation
Cl.Cl.Cl.Cl.[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[CH:20]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:19][CH2:18]3)=[O:14])=[CH:8][C:7]=1[NH:30][C:31]1[N:36]=[C:35]([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)[CH:34]=[CH:33][N:32]=1.C(N(CC)CC)C.[CH3:50][C:51]([CH3:53])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C>[CH:51]([N:27]1[CH2:26][CH2:25][N:24]([CH:20]2[C:21]3[C:17](=[CH:16][C:15]([C:13]([NH:12][C:9]4[CH:10]=[CH:11][C:6]([CH3:5])=[C:7]([NH:30][C:31]5[N:36]=[C:35]([C:37]6[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=6)[CH:34]=[CH:33][N:32]=5)[CH:8]=4)=[O:14])=[CH:23][CH:22]=3)[CH2:18][CH2:19]2)[CH2:29][CH2:28]1)([CH3:53])[CH3:50]

Participants

6

Reactant 4

HCID 180AcetoneHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 67457633HCID 67457633, compound

Product 1

HCID 46831268HCID 46831268, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(4-Methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl)-1-piperazin-1-yl-2,3-dihydro-1H-indene-5-carboxamide tetrahydrochloride (100 mg, 0.15 mmol) was dissolved in DMF (2 mL), and triethylamine (101 mg, 1 mmol) was added followed by acetone (35 mg, 0.6 mmol). After the solution was stirred for 20 minutes, sodium triacetoxyborohydride (128 mg, 0.6 mmol) was added. The solution obtained was stirred overnight at room temperature and then purified by high performance liquid chromatography at pH=10 to obtain 58 mg (71% yield) of the title compound. MS (M+1)=548.31. 1HNMR (DMSO-d6, ppm): δ 10.14 (s, 1H); 9.26 (s, 1H); 8.98 (s, 1H); 8.67 (d, J=4.8 Hz, 1H); 8.49 (d, J=4.8 Hz, 1H); 8.46 (d, J=8.4 Hz); 8.05 (s, 1H); 7.77 (s, 1H); 7.74 (d, J=8.0 Hz, 1H); 7.51 (dd, J=8.0 & 4.8 Hz, 4.8 Hz, 1H); 7.46 (d, J=8.2 Hz, 1H); 7.41 (d, J=5.2 Hz, 1H); 7.35 (d, J=7.6 Hz, 1H); 7.17 (d, J=8.4 Hz, 1H); 4.30 (t, J=7.0 Hz, 1H); 2.91 (m, 12H); 2.81 (s, 3H); 2.3-2.6 (m, 9H); 2.02 (m, 2H); 0.92 (t, J=6.4 Hz, 6H).

Workup

  1. customThe solution obtained
  2. stirringwas stirred overnight at room temperature
  3. custompurified by high performance liquid chromatography at pH=10

Sources & evidence

ORD record
ord-9438a2af184b43138983282d97f42e3e
Source dataset
uspto-grants-2014_04
Patent number
US08703771B2

Reaction notes

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