Diisopropylethylamine → HCID 22258331, compound

HRID 1047199Notes

Reaction equation

HRID 1047199 reaction equation
Cl.[CH:2]1([CH2:5][CH:6]2[C:15]3[C:10](=[CH:11][C:12]([F:16])=[CH:13][CH:14]=3)[CH2:9][CH2:8][CH:7]2[NH2:17])[CH2:4][CH2:3]1.C1([O:24][C:25](=O)[NH:26][C:27]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:28]=2[CH:29]=[CH:30][N:31]=[CH:32]3)C=CC=CC=1.C(N(C(C)C)CC)(C)C>CS(C)=O>[CH:2]1([CH2:5][CH:6]2[C:15]3[C:10](=[CH:11][C:12]([F:16])=[CH:13][CH:14]=3)[CH2:9][CH2:8][CH:7]2[NH:17][C:25]([NH:26][C:27]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:28]=2[CH:29]=[CH:30][N:31]=[CH:32]3)=[O:24])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11380046Phenyl isoquinolin-5-ylcarbamateHCID 22258334HCID 22258334, compound

Product 1

HCID 22258331HCID 22258331, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-Cyclopropylmethyl-6-fluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydrochloride (127 mg, 0.49 mmol), isoquinolin-5-yl-carbamic acid phenyl ester (150 mg, 0.49 mmol), and diisopropylethylamine (193 mg, 1.47 mmol) were combined and stirred at ambient temperature in DMSO (3 mL) overnight. The product was purified by directly injecting the crude reaction onto a reverse phase prep-HPLC (10-90% water:acetonitrile gradient). The appropriate fractions were lyophilized to yield 1-(1-cyclopropylmethyl-6-fluoro-1,2,3,4-tetrahydro-naphthalen-2-yl)-3-isoquinolin-5-yl-urea 71 (68 mg, 0.14 mmol). MS (MH+) 390; 1H NMR (CD3OD) δ 0.08-0.87 (m, 2H), 1.60-1.65 (m, 2H), 2.03 (m, 1H), 2.97 (m, 2H), 3.14 (m, 1H), 4.36 (m, 1H), 6.87 (m, 2H), 7.27 (m, 1H), 7.93 (t, 1H, J=2.6 Hz), 8.14 (d, 1H, J=2.7 Hz), 8.32 (d, 1H, J=2.2 Hz), 8.47 (d, 1H, J=2.6 Hz), 8.53 (d, 1H, J=2.2 Hz), 9.63 (s, 1H). HPLC Rt=3.63 min (10-90% water:acetonitrile gradient, 100% pure).

Workup

  1. customThe product was purified
  2. customreaction onto a reverse phase prep-HPLC (10-90% water:acetonitrile gradient)

Sources & evidence

ORD record
ord-276c52835e6b459b979bd2ecb8d37162
Source dataset
uspto-grants-2013_10
Patent number
US08569505B2

Reaction notes

Loading…