Sodium hydride → HCID 117729265, compound

HRID 2200063Notes

Reaction equation

HRID 2200063 reaction equation
[H-].[Na+].[NH2:3][C@@H:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C@H:7]([OH:14])[CH2:6][CH2:5]1.F[C:16]1[CH:17]=[CH:18][C:19]2[N:20]([C:22]([C@H:25]3[N:29]([CH3:30])[CH2:28][C@@H:27]([N:31]([CH3:33])[CH3:32])[CH2:26]3)=[N:23][N:24]=2)[CH:21]=1>CN(C=O)C>[NH2:3][C@@H:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C@H:7]([O:14][C:16]2[CH:17]=[CH:18][C:19]3[N:20]([C:22]([C@H:25]4[N:29]([CH3:30])[CH2:28][C@@H:27]([N:31]([CH3:33])[CH3:32])[CH2:26]4)=[N:23][N:24]=3)[CH:21]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 86686674(1R,4S)-4-Amino-1,2,3,4-tetrahydronaphthalen-1-olHCID 117728921HCID 117728921, compound

Product 1

HCID 117729265HCID 117729265, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of sodium hydride (60% dispersion in oil, 548 mg, 14.6 mmol) in dry DMF (10.0 mL) under nitrogen was treated with Intermediate 1 (800 mg, 4.9 mmol) and the mixture was stirred for 20 min. Intermediate 38c (1.28 g, 4.6 mmol) was added and the mixture was stirred at RT for 4 hours then quenched with MeOH. The mixture was further diluted with MeOH and applied to a pre-conditioned (MeOH) SCX-2 cartridge (25 g). The cartridge was eluted with MeOH then 2M NH3 in MeOH. The relevant product containing fractions were combined and concentrated in vacuo to give the title compound as a dark brown oil (1.8 g, 86%). LCMS (Method 3): Rt 0.6, m/z 407 [MH+].

Workup

  1. stirringthe mixture was stirred at RT for 4 hours
  2. customthen quenched with MeOH
  3. additionThe mixture was further diluted with MeOH
  4. washThe cartridge was eluted with MeOH
  5. additionThe relevant product containing fractions
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf44b35770ba4130ab80948b2cbcc079
Source dataset
uspto-grants-2016_06
Patent number
US09359354B2

Reaction notes

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