Dimethylformamide → HCID 86660687, compound

HRID 2368773Notes

Reaction equation

HRID 2368773 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](N2CCNCC2)[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:45]([CH2:48][CH3:49])[CH2:46][CH3:47])C.[C:50]([O:53][BH-](OC(=O)C)OC(=O)C)(=O)[CH3:51].[Na+].C[N:65](C=O)C>>[OH:53][CH2:50][CH2:51][CH:47]1[CH2:46][NH:45][CH2:48][CH2:49][N:65]1[C:16]1[C:15]([C:13]([NH:12][C:9]2[CH:10]=[CH:11][C:6]([CH3:5])=[C:7]([NH:30][C:31]3[N:36]=[C:35]([C:37]4[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=4)[CH:34]=[CH:33][N:32]=3)[CH:8]=2)=[O:14])=[CH:23][CH:22]=[C:21]2[C:17]=1[CH2:18][CH2:19][CH2:20]2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 67457633HCID 67457633, compound

Product 1

HCID 86660687HCID 86660687, compoundYield 46%

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 {[tert-butyl(dimethyl)silyl]oxo}acetaldehyde (100 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. The dried product was dissolved in 2 mL of methylene chloride/2 ml trifluoroacetic acid. The solution was concentrated after being stirred overnight and purified by high performance liquid chromatography at pH=10 to obtain 38 mg (46% yield) of the title compound. MS (M+1)=550.29. 1HNMR (DMSO-d6, ppm): δ 10.16 (s, 1H); 9.23 (s, 1H); 8.97 (s, 1H); 8.65 (d, J=4.4 Hz, 1H); 8.48 (d, J=6.0 Hz, 1H); 8.46 (d, J=4.8 Hz); 8.02 (s, 1H); 7.82 (m, 2H); 7.51 (m, 1H); 7.40 (m, 2H); 7.14 (d, J=8.4 Hz, 1H); 2.6-3.7 (m, 17H); 2.16 (s, 3H).

Workup

  1. customThe solution obtained
  2. stirringwas stirred overnight at room temperature
  3. custompurified by high performance liquid chromatography
  4. dissolutionThe dried product was dissolved in 2 mL of methylene chloride/2 ml trifluoroacetic acid
  5. concentrationThe solution was concentrated
  6. stirringafter being stirred overnight
  7. custompurified by high performance liquid chromatography at pH=10

Sources & evidence

ORD record
ord-c8d3c1eaf91b43e584f422577b1c2521
Source dataset
uspto-grants-2014_04
Patent number
US08703771B2

Reaction notes

Loading…