Diisopropylethylamine → HCID 22258331, compound

HRID 1610916Notes

Reaction equation

HRID 1610916 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-bbce73ce3f6942c9b832862f706d9f7f
Source dataset
uspto-grants-2006_01
Patent number
US06984647B2

Reaction notes

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