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N-methyl-2-pyrrolidone → 2-{4-[(S)-7-(3-Fluoro-propyl)-2,7-diaza-spiro[4.4]non-2-yl]-phenyl}-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one

HRID 69442
Notes
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Reaction equation

HRID 69442 reaction equation
[CH2:1]1[C@@:5]2([CH2:9][CH2:8][NH:7][CH2:6]2)[CH2:4][CH2:3][N:2]1[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([OH:26])[CH:22]=3)[C:17]2=[O:27])=[CH:12][CH:11]=1.Br[CH2:29][CH2:30][CH2:31][F:32].C(=O)([O-])O.[Na+].CN1C(=O)CCC1>O.C(OCC)(=O)C>[F:32][CH2:31][CH2:30][CH2:29][N:7]1[CH2:8][CH2:9][C@@:5]2([CH2:1][N:2]([C:10]3[CH:15]=[CH:14][C:13]([N:16]4[CH2:25][CH2:24][C:23]5[C:18](=[CH:19][CH:20]=[C:21]([OH:26])[CH:22]=5)[C:17]4=[O:27])=[CH:12][CH:11]=3)[CH2:3][CH2:4]2)[CH2:6]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 67699Propane, 1-bromo-3-fluoro-HCID 516892Sodium BicarbonateHCID 689918082-[(S)-4-(2,7-Diaza-spiro[4.4]non-2-yl)-phenyl]-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one

Product 1

HCID 689903662-{4-[(S)-7-(3-Fluoro-propyl)-2,7-diaza-spiro[4.4]non-2-yl]-phenyl}-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-[(S)-4-(2,7-diaza-spiro[4.4]non-2-yl)-phenyl]-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one (0.20 g), 1-bromo-3-fluoro-propane (76 mg), sodium hydrogencarbonate (10 mg) and NMP (5 mL) was heated at 50° C. for 15 hours. The reaction mixture was distributed between ethyl acetate and water. The organic phase was dried over magnesium sulfate and concentrated. The raw product was purified by preparative HPLC. In this way the product was obtained with molecular weight 423.54 (C25H30FN3O2); MS (ESI): 424 (M+H+).

Workup

  1. dry with materialThe organic phase was dried over magnesium sulfate
  2. concentrationconcentrated
  3. customThe raw product was purified by preparative HPLC
  4. customIn this way the product was obtained with molecular weight 423.54 (C25H30FN3O2)

Sources & evidence

ORD record
ord-66e9a8fd87d04aea8e26a46ce96c38f2
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822495B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes