Hydrochloric Acid → HCID 57814620, compound

HRID 1425541Notes

Reaction equation

HRID 1425541 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 35Cl79Br, 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-3dc0b60e037a4a07a4257c684a728bf2
Source dataset
uspto-grants-2015_01
Patent number
USRE045336E1

Reaction notes

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