Acetyl chloride → HCID 46831270, compound

HRID 2368774Notes

Reaction equation

HRID 2368774 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.[C:50](Cl)(=[O:52])[CH3:51]>CN(C=O)C>[C:50]([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)(=[O:52])[CH3:51]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67457633HCID 67457633, compound

Product 1

HCID 46831270HCID 46831270, compoundYield 55%

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 acetyl chloride (16 mg, 0.2 mmol) while being cooled in an ice bath. After being stirred for 20 minutes, the solution obtained was purified by high performance liquid chromatography at pH=10 to obtain 45 mg (55% yield) of the title compound. MS (+1)=548.27. 1HNMR (DMSO-d6, ppm): δ 10.15 (s, 1H); 9.26 (s, 1H); 8.99 (s, 1H); 8.66 (d, J=4.8 Hz, 1H); 8.49 (d, J=5.2 Hz, 1H); 8.45 (d, J=8.4 Hz); 8.05 (s, 1H); 7.79 (s, 1H); 7.76 (d, J=8.0 Hz, 1H); 7.50 (dd, J=8.0 & 4.8 Hz, 1H); 4.37 (t, J=7.0 Hz, 1H); 3.42 (m, 1H); 3.40 (m, 3H); 2.91 (m, 1H); 2.83 (m, 1H); 2.2-2.5 (m, 4H); 2.20 (s, 3H); 2.06 (m, 2H); 1.95 (s, 3H).

Workup

  1. temperaturewhile being cooled in an ice bath
  2. customthe solution obtained
  3. customwas purified by high performance liquid chromatography at pH=10

Sources & evidence

ORD record
ord-b7fa202c4bca44f29104c125326216e8
Source dataset
uspto-grants-2014_04
Patent number
US08703771B2

Reaction notes

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