Hydrochloric Acid → HCID 57814620, compound

HRID 1183904Notes

Reaction equation

HRID 1183904 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][CH2:8][NH:9]C(=O)OC(C)(C)C)=[C:4]([C:19]2[N:23]([CH3:24])[N:22]=[CH:21][C:20]=2[Br:25])[CH:3]=1.[Cl:26][C:27]1[CH:35]=[C:34]2[C:30]([CH2:31][CH2:32][NH:33]2)=[CH:29][CH:28]=1.Cl.CN([CH:40]=[O:41])C>>[NH2:9][CH2:8][CH2:7][O:6][C:5]1[CH:17]=[CH:18][C:2]([NH:1][C:40]([N:33]2[C:34]3[C:30](=[CH:29][CH:28]=[C:27]([Cl:26])[CH:35]=3)[CH2:31][CH2:32]2)=[O:41])=[CH:3][C:4]=1[C:19]1[N:23]([CH3:24])[N:22]=[CH:21][C:20]=1[Br:25]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 2585676-Chloro-2,3-dihydro-1h-indoleHCID 67265391HCID 67265391, compound

Product 1

HCID 57814620HCID 57814620, compoundYield 20.1%

Procedure

A mixture of tert-butyl 2-(4-amino-2-(4-bromo-1-methyl-1H-pyrazol-5-yl)phenoxy)ethylcarbamate (30 mg, 54 μmol) and 6-chloroindoline (8.3 mg, 54 μmol) in 1 mL of DMF was stirred at room temperature overnight. Then to the mixture was added 1 mL of 2M HCl. The mixture was stirred at room temperature overnight. The mixture was concentrated and the crude product was subjected to purification on HPLC. The proper fractions were collected and lyophilized to afford yellow oil in 20.1% yield. LCMS m/z (%)=492 (M+H 35Cl 79Br, 100). 1H NMR (400 MHz, MeOD) δ ppm 3.1 (m, 4 H), 3.7 (s, 3 H), 4.1 (m, 3 H), 4.2 (m, 1 H), 6.8 (dd, J=7.6, 2.0 Hz, 1 H), 7.1 (d, J=7.6 Hz, 1 H), 7.1 (d, J=9.1 Hz, 1 H), 7.3 (d, J=3.0 Hz, 1 H), 7.5 (s, 1 H), 7.6 (dd, J=9.1, 2.5 Hz, 1 H), 7.8 (d, J=2.0 Hz, 1 H).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. concentrationThe mixture was concentrated
  3. customthe crude product was subjected to purification on HPLC
  4. customThe proper fractions were collected
  5. customto afford yellow oil in 20.1% yield

Sources & evidence

ORD record
ord-e267e875cedd4f70b25aeb89c688bc43
Source dataset
uspto-grants-2014_03
Patent number
US08664258B2

Reaction notes

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