Sodium Hydroxide → HCID 10071063, compound

HRID 1047198Notes

Reaction equation

HRID 1047198 reaction equation
C1(O[C:8](=[O:20])[NH:9][C:10]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:11]=2[CH:12]=[CH:13][N:14]=[CH:15]3)C=CC=CC=1.NC1C2C(=CC=CC=2)CCC1.[CH2:32]([CH:39]1[C:48]2[C:43](=[CH:44][C:45]([F:49])=[CH:46][CH:47]=2)[CH2:42][CH2:41][CH:40]1[NH2:50])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[OH-].[Na+]>CS(C)=O.O>[CH2:32]([CH:39]1[C:48]2[C:43](=[CH:44][C:45]([F:49])=[CH:46][CH:47]=2)[CH2:42][CH2:41][CH:40]1[NH:50][C:8]([NH:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][N:14]=[CH:15]2)=[O:20])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 180661,2,3,4-Tetrahydro-1-naphthylamineHCID 11380046Phenyl isoquinolin-5-ylcarbamateHCID 22258318HCID 22258318, compound

Product 1

HCID 10071063HCID 10071063, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Isoquinolin-5-yl-carbamic acid phenyl ester 2-1 (0.005 mole, 1.32 g) was dissolved in 15 mL of DMSO (dimethylsulfoxide) followed by the addition of the aminotetralin 2-2, 1-benzyl-6-fluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamine (0.0044 mole, 1.12 g). The reaction mixture was then stirred at room temperature for 16 hours. The reaction mixture was poured into 50 mL of water containing 10 mL of 1N NaOH (sodium hydroxide). The precipitated solid was collected by filtration. This solid was chromatographed on silica gel eluting with methylene chloride, 3% methanol. Subsequently the product was further purified by recrystallization from ethyl acetate. The title compound 38, (1-(1-benzyl-6-fluoro-1,2,3,4-tetrahydro-naphthalen-2-yl)-3-isoquinolin-5-yl-urea) was obtained as an off-white solid (1.25 g, 0.00295 mole). MS (MH+): 426; 1H NMR (MeOH): δ 1.35 (m, 1H), 1.9 (m, 1H), 2.1-2.2 (m, 1H), 2.9-3.1 (m, 4H) 3.45 (m, 1H), 4.1-4.2 (m, 1H), 6.7 (t, 1H), 6.8-6.9 (m, 2H), 7.1-7.3 (m, 5H), 7.85 (t, 1H), 8.1 (d, 1H), 8.25 (d, 1H), 8.35 (d, 1H), 8.6 (d, 1H).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. customThis solid was chromatographed on silica gel eluting with methylene chloride, 3% methanol
  3. customSubsequently the product was further purified by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-d325985ad3bf457b903c36d6e96f1ec0
Source dataset
uspto-grants-2013_10
Patent number
US08569505B2

Reaction notes

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