Hydrochloric Acid → HCID 178467078, compound

HRID 2271685Notes

Reaction equation

HRID 2271685 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@H:16]1[CH2:21][CH2:20][C@H:19]([CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH2:18][CH2:17]1.[Cl:27][C:28]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[C:30]([Cl:43])[C:29]=1[OH:44].Cl>CO>[ClH:27].[Cl:27][C:28]1[CH:33]=[C:32]([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@H:16]2[CH2:21][CH2:20][C@H:19]([CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH2:18][CH2:17]2)[CH:31]=[C:30]([Cl:43])[C:29]=1[OH:44]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 667151272,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 178467065HCID 178467065, compound

Product 1

HCID 178467078HCID 178467078, compoundYield 108.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following general procedure F, 1-(6-bromo-4-(trans-4-(2-(dimethylamino)ethyl)cyclohexyl amino)quinolin-3-yl)ethanone (4.8 g, 11.5 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (3.8 g, 13.1 mmol) to obtain the free base. The purified product was suspended in methanol (100 mL) after which HCl (125 mL, 1.25 M in methanol) was added to form a solution. The solution was concentrated to ˜50 mL and the resultant solid was filtered, washed with methanol, and dried to obtain desired product (3.8 g, 58% over two steps) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ 9.10 (s, 1H), 8.50 (s, 1H), 8.27 (dd, J=8.8, 1.8 Hz, 1H), 7.97 (d, J=8.8 Hz, 1H), 7.73 (s, 2H), 4.55-4.48 (m, 1H), 3.27-3.15 (m, 2H), 2.90 (s, 6H), 2.74 (s, 3H), 2.42 (br d, J=12.3 Hz, 2H), 2.04 (br d, J=12.9 Hz, 2H), 1.84-1.65 (m, 4H), 1.63-1.56 (m, 1H), 1.34 (q, J=12.3 Hz, 2H); ESI MS m/z 500 [C27H31Cl2N3O2+H]+; HPLC>99% (AUC), tR=6.87 min.

Workup

  1. customto obtain the free base
  2. additionwas added
  3. customto form a solution
  4. concentrationThe solution was concentrated to ˜50 mL
  5. filtrationthe resultant solid was filtered
  6. washwashed with methanol
  7. customdried

Sources & evidence

ORD record
ord-3d42e9faa34743cc84fde2525b55e979
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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