HCID 46830969, compound → HCID 46830970, compound

HRID 2368770Notes

Reaction equation

HRID 2368770 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[CH:16]([N:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]2)[CH2:15][CH2:14]3)=[O:10])=[CH:4][C:3]=1[NH:33][C:34]1[N:39]=[C:38]([C:40]2[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=2)[CH:37]=[CH:36][N:35]=1>Cl.O1CCOCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[CH:16]([N:20]2[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]2)[CH2:15][CH2:14]3)=[O:10])=[CH:4][C:3]=1[NH:33][C:34]1[N:39]=[C:38]([C:40]2[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=2)[CH:37]=[CH:36][N:35]=1

Participants

4

Reactant 1

HCID 46830969HCID 46830969, compound

Product 1

HCID 46830970HCID 46830970, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-{5-[({4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl}amino)carbonyl]-2,3-dihydro-1H-inden-1-yl}piperazin-1-carboxylate (2 g, 3.3 mmol) was dissolved in 4 N HCl in dioxane (10 mL). The solution was concentrated to obtain the solid product after being stirred at room temperature for 3 hours. The product (100 mg) was purified by high performance liquid chromatography at pH=10 to obtain the subtitle compound. MS (M+1)=506.26. 1HNMR (DMSO-d6, ppm): δ 10.08 (s, 1H); 9.20 (s, 1H); 8.93 (s, 1H); 8.62 (d, J=4.8 Hz, 1H); 8.44 (d, J=5.2 Hz, 1H); 8.40 (d, J=8.0 Hz, 1H); 8.00 (s, 1H); 7.72 (s, 1H); 7.70 (d, J=8.0 Hz, 1H); 7.45 (dd, J=8.2 Hz, 4.8 Hz, 1H); 7.41 (d, J=8.2 Hz, 1H); 7.36 (d, J=5.2 Hz, 1H); 7.31 (d, J=8.0 Hz, 1H); 7.12 (d, J=8.8 Hz, 1H); 4.22 (t, J=6.8 Hz, 1H); 2.80 (m, 2H); 2.60 (m, 4H); 2.35 (m, 2H); 2.22 (m, 2H); 2.15 (s, 3H); 2.00 (m, 2H).

Workup

  1. concentrationThe solution was concentrated
  2. customto obtain the solid product
  3. customThe product (100 mg) was purified by high performance liquid chromatography at pH=10

Sources & evidence

ORD record
ord-4de3ca61254f4d869a7dcf12a54b7df5
Source dataset
uspto-grants-2014_04
Patent number
US08703771B2

Reaction notes

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