Sodium hydride → HCID 86687049, compound

HRID 2285016Notes

Reaction equation

HRID 2285016 reaction equation
[NH2:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@@H:5]([OH:12])[CH2:4][CH2:3]1.[H-].[Na+].F[C:16]1[CH:17]=[CH:18][C:19]2[N:20]([C:22]([N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[N:23][N:24]=2)[CH:21]=1>CN(C=O)C>[N:25]1([C:22]2[N:20]3[CH:21]=[C:16]([O:12][C@@H:5]4[C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[C@@H:2]([NH2:1])[CH2:3][CH2:4]4)[CH:17]=[CH:18][C:19]3=[N:24][N:23]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 86686682(1S,4S)-4-amino-1,2,3,4-tetrahydronaphthalen-1-olHCID 86686951HCID 86686951, compound

Product 1

HCID 86687049HCID 86687049, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Intermediate B (74.0 mg, 454 μmol) was added to a mixture of NaH (60% in mineral oil, 27.2 mg, 681 μmol) in DMF (2.5 mL) at RT and stirred for 15 min. Intermediate 3b (100 mg, 454 μmol) was then added and the resulting mixture heated to 60° C. for 1 h. After cooling, the reaction was quenched with sat. aq. NH4Cl solution. The mixture was diluted with water and extracted with EtOAc. The combined organic extracts were concentrated in vacuo. The resulting residue was purified by FCC, using 0 to 10% [2M NH3 in MeOH] in DCM, to afford the title compound as an orange residue (122 mg, 74%). LCMS (Method 3): Rt 2.13 min, m/z 364 [MH+].

Workup

  1. temperatureAfter cooling
  2. customthe reaction was quenched with sat. aq. NH4Cl solution
  3. additionThe mixture was diluted with water
  4. extractionextracted with EtOAc
  5. concentrationThe combined organic extracts were concentrated in vacuo
  6. customThe resulting residue was purified by FCC

Sources & evidence

ORD record
ord-b3ce70b6bd744e25bb829dbee09a2cf3
Source dataset
uspto-grants-2015_09
Patent number
US09145413B2

Reaction notes

Loading…