HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Tetrahydrofuran → HCID 44160016, compound

HRID 1926304
Notes
Print preview

Reaction equation

HRID 1926304 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH:13]3[CH2:18][CH2:17][N:16]([CH:19]=O)[CH2:15][CH2:14]3)[CH:12]=2)=[CH:4][C:3]=1[C:21]1[N:22]=[CH:23][C:24]2[C:29]([CH:30]=1)=[C:28]([Cl:31])[CH:27]=[CH:26][C:25]=2[F:32].C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOC(C)=O>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([F:32])=[C:24]2[C:29]=1[CH:30]=[C:21]([C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([C:8]3[CH:9]=[N:10][N:11]([CH:13]4[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]4)[CH:12]=3)[CH:4]=1)[N:22]=[CH:23]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 866331564-{4-[6-Amino-5-(5-chloro-8-fluoroisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carbaldehyde

Product 1

HCID 44160016HCID 44160016, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-{4-[6-amino-5-(5-chloro-8-fluoroisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carbaldehyde (50.0 mg, 0.111 mmol) in THF (5 mL, 60 mmol), cooled to ≈0° C., LiAlH4 (1.0M solution in THF; 0.27 mL, 0.27 mmol) was added, and the reaction mixture was stirred at 0° C.→rt for 30 min. Sodium sulfate decahydrate (0.1 g, 0.4 mmol) and EtOAc were added and the reaction mixture was stirred for 10 min at rt. The solids were filtered off, and the filtrate was concentrated and purified on prep-TLC eluting with 5% 7M NH3 (MeOH)/DCM to give the title compound as pale yellow oil. MS (ES+): m/z=436.79/438.74 [MH+]. HPLC: tR=2.24 min (ZQ2, polar—5 min).

Workup

  1. stirringthe reaction mixture was stirred for 10 min at rt
  2. filtrationThe solids were filtered off
  3. concentrationthe filtrate was concentrated
  4. custompurified
  5. washon prep-TLC eluting with 5% 7M NH3 (MeOH)/DCM

Sources & evidence

ORD record
ord-7127344ba85744ccbc2bd3f23052e9e6
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178668B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes