Sodium Bicarbonate → HCID 11317113, compound

HRID 2244128Notes

Reaction equation

HRID 2244128 reaction equation
C1(O[C:8](=[O:21])[NH:9][C:10]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:11]=2[CH:12]=[CH:13][N:14]=[C:15]3[Cl:20])C=CC=CC=1.Cl.[CH2:23]([CH:30]1[C:39]2[C:34](=[CH:35][C:36]([F:40])=[CH:37][CH:38]=2)[CH2:33][CH2:32][CH:31]1[NH2:41])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)(O)[O-].[Na+]>CS(C)=O>[CH2:23]([CH:30]1[C:39]2[C:34](=[CH:35][C:36]([F:40])=[CH:37][CH:38]=2)[CH2:33][CH2:32][CH:31]1[NH:41][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]=[C:15]2[Cl:20])=[O:21])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 222583171-Benzyl-6-fluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydrochlorideHCID 71382112Phenyl (1-chloroisoquinolin-5-yl)carbamate

Product 1

HCID 11317113HCID 11317113, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(1-Chloro-isoquinolin-5-yl)-carbamic acid phenyl ester (150 mgs, 0.5 mmol), 1-Benzyl-6-fluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydrochloride (146 mgs, 0.5 mmol), and sodium bicarbonate (42 mgs, 0.5 mmol) were combined and stirred for one hour in DMSO (4 ml) at ambient temperature. 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-Benzyl-6-fluoro-1,2,3,4-tetrahydro-naphthalen-2-yl)-3-(1-chloro-isoquinolin-5-yl)-urea (64 mgs, 28%) MS (MH+) 459; 1H NMR (CD3OD) δ 1.93-2.06 (m, 1H), 2.09-2.13 (m, 1H), 2.91-3.07 (m, 4H), 3.40-3.42 (m, 1H), 4.07-4.10 (s, 1H), 6.69-6.78 (m, 1H), 6.80-6.89 (m, 2H), 7.12-7.26 (m, 5H), 7.72 (t, 1H, J=8.2 Hz), 7.83 (d, 1H, J=6.1 Hz), 8.19 (d, 1H, J=8.6 Hz), 8.17-8.24 (m, 2H). HPLC Rt=4.04 min (50-90% 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-ddc2b8eb14704712a7f6a5a0461b1e92
Source dataset
uspto-grants-2010_03
Patent number
US07678812B2

Reaction notes

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