1-Hydroxybenzotriazole → HCID 89726875, compound

HRID 926361Notes

Reaction equation

HRID 926361 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:15]([OH:17])=O)[N:9]2[CH2:14][CH2:13][O:12][CH2:11][C:10]=12)=[O:5])[CH3:2].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[F:40][C:41]1[CH:46]=[CH:45][C:44]([C@H:47]([NH2:49])[CH3:48])=[CH:43][CH:42]=1>CN(C)C=O.O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:15](=[O:17])[NH:49][C@@H:47]([C:44]2[CH:45]=[CH:46][C:41]([F:40])=[CH:42][CH:43]=2)[CH3:48])[N:9]2[CH2:14][CH2:13][O:12][CH2:11][C:10]=12)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6950187(1R)-(+)-1-(4-Fluorophenyl)ethylamineHCID 89726819HCID 89726819, compound

Product 1

HCID 89726875HCID 89726875, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6,8-dicarboxylic acid 8-ethyl ester (Comp. No. 5a) (6.09 g, 25.5 mmol) in dimethylformamide (60 ml) was added 1-hydroxybenzotriazole (3.785 g, 0.028 mol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.37 g, 28 mmol). The mixture was stirred for 90 min at 50° C., then (R)-1-(4-fluoro-phenyl)ethylamine (3.9 g, 28 mmol) was added and the mixture was stirred at 25° C. overnight. An excess of water was added, the solid which precipitated was filtered off, washed with a small amount of water to give 9.0 g (98%) of 6-[(R)-1-(4-fluoro-phenyl)-ethylcarbamoyl]-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ethyl ester.

Workup

  1. stirringthe mixture was stirred at 25° C. overnight
  2. customthe solid which precipitated
  3. filtrationwas filtered off
  4. washwashed with a small amount of water

Sources & evidence

ORD record
ord-f563d66c304f493fa93446fcf148cf8a
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Reaction notes

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