Acetaldehyde → HCID 46830971, compound

HRID 2368771Notes

Reaction equation

HRID 2368771 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.[CH2:43](N(CC)CC)[CH3:44].C(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C>[CH2:43]([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)[CH3:44]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 67457633HCID 67457633, compound

Product 1

HCID 46830971HCID 46830971, compoundYield 63%

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 acetaldehyde (26 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 50 mg (63% yield) of the title compound. MS (M+1)=523.29. 1HNMR (DMSO-d6, ppm): δ 10.14 (s, 1H); 9.25 (s, 1H); 8.98 (s, 1H); 8.67 (d, J=4.8 Hz, 1H); 8.49 (d, J=5.2 Hz, 1H); 8.46 (d, J=8.6 Hz, 1H); 8.05 (s, 1H); 7.77 (s, 1H); 7.75 (d, J=8.8 Hz, 1H); 7.50 (dd, J=8.0 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=8.8 Hz, 1H); 4.31 (t, J=6.8 Hz, 1H); 2.2-3.0 (m, 12H); 2.20 (s, 3H); 2.03 (m, 2H); 0.95 (t, J=7.0 Hz, 3H).

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-2620d035200a4fdaa91bf4fc2058c5a7
Source dataset
uspto-grants-2014_04
Patent number
US08703771B2

Reaction notes

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