Hydrochloric Acid → HCID 66716385, compound

HRID 2271687Notes

Reaction equation

HRID 2271687 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]2[NH:15][C:16]1[CH:17]=[N:18][C:19]([O:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])=[CH:20][CH:21]=1.[Cl:28][C:29]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[C:31]([Cl:44])[C:30]=1[OH:45].Cl>ClCCl.CO>[ClH:28].[Cl:28][C:29]1[CH:34]=[C:33]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]3[NH:15][C:16]2[CH:17]=[N:18][C:19]([O:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])=[CH:20][CH:21]=2)[CH:32]=[C:31]([Cl:44])[C:30]=1[OH:45]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 667151272,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 66715674HCID 66715674, compound

Product 1

HCID 66716385HCID 66716385, compoundYield 146%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Following general procedure F, 1-(6-bromo-4-(6-(2-(dimethylamino)ethoxy)pyridin-3-ylamino)quinolin-3-yl)ethanone (5.0 g, 12.0 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (3.7 g, 13.0 mmol) to obtain the free base. The purified product was suspended in dichloromethane/methanol (1:1, 300 mL) after which HCl (30 mL, 1.25 M in methanol) was added to form a solution. The solution was concentrated to dryness to obtain desired product (5.2 g, 74% over two steps) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ 9.27 (s, 1H), 8.29 (d, J=2.9 Hz, 1H), 8.20-8.10 (m, 1H), 8.06-7.96 (m, 1H), 7.87-7.77 (m, 2H), 7.20 (s, 2H), 7.17-7.08 (m, 1H), 4.81-4.71 (m, 2H), 3.64 (t, J=5.1 Hz, 2H), 3.01 (s, 6H), 2.80 (s, 3H); ESI MS m/z 511 [C26H24Cl2N4O3+H]+; HPLC>99% (AUC), tR=6.86 min.

Workup

  1. customto obtain the free base
  2. additionwas added
  3. customto form a solution
  4. concentrationThe solution was concentrated to dryness

Sources & evidence

ORD record
ord-9156c9df49a042fc9c06f01950f3e99d
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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