Ammonia → HCID 86687028, compound

HRID 2282443Notes

Reaction equation

HRID 2282443 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]([CH3:31])[CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])=[N:23][N:24]=2)[CH:21]=1.N>CN(C=O)C.CO.C(Cl)Cl>[NH2:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@H:5]([O:12][C:16]2[CH:17]=[CH:18][C:19]3[N:20]([C:22]([N:25]([CH3:31])[CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])=[N:23][N:24]=3)[CH:21]=2)[CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 24758Sodium hydrideHCID 86686674(1R,4S)-4-Amino-1,2,3,4-tetrahydronaphthalen-1-olHCID 89612236N-(6-Fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-N,N',N'-trimethyl-ethane-1,2-diamine

Product 1

HCID 86687028HCID 86687028, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Intermediate A (143 mg, 0.88 mmol) in DMF (3 mL) was added NaH (60% in oil, 96 mg, 2.4 mmol) and the mixture stirred at RT for 20 min, before Intermediate 43a (190 mg, 0.80 mmol) was added. This mixture was heated at 60° C. in the microwave for 1 h. The reaction mixture was applied to an SCX-2 cartridge and washed with MeOH. The product was eluted with 2M NH3 in MeOH; concentration in vacuo gave a residue. FCC, using 0-20% [2M NH3 in MeOH] in DCM, gave the title compound as a pale brown oil (140 mg, 46%). LCMS (Method 1): Rt 1.34 min, ink 381 [MH+].

Workup

  1. additionwas added
  2. washwashed with MeOH
  3. washThe product was eluted with 2M NH3 in MeOH
  4. concentrationconcentration in vacuo
  5. customgave a residue

Sources & evidence

ORD record
ord-1f9a190adad24d85adbe60930c6d04b9
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

Loading…