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Ammonia → (1S,4R)-4-[3-((S)-1,2-Dimethyl-pyrrolidin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-ylamine

HRID 2285004
Notes
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Reaction equation

HRID 2285004 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@:3]1([C:8]1[N:12]2[CH:13]=[C:14](F)[CH:15]=[CH:16][C:11]2=[N:10][N:9]=1)[CH3:7].[NH2:18][C@@H:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:22]([OH:29])[CH2:21][CH2:20]1.[H-].[Na+].N>CN(C=O)C.CO.C(Cl)Cl>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@:3]1([C:8]1[N:12]2[CH:13]=[C:14]([O:29][C@H:22]3[C:23]4[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=4)[C@@H:19]([NH2:18])[CH2:20][CH2:21]3)[CH:15]=[CH:16][C:11]2=[N:10][N:9]=1)[CH3:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 222AmmoniaHCID 24758Sodium hydrideHCID 86686674(1R,4S)-4-Amino-1,2,3,4-tetrahydronaphthalen-1-olHCID 86687034HCID 86687034, compound

Product 1

HCID 86687035(1S,4R)-4-[3-((S)-1,2-Dimethyl-pyrrolidin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-ylamineYield 75%

Reagents, catalysts & solvents

3
HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Intermediate 47b (150 mg, 0.64 mmol) and Intermediate A (126 mg, 0.64 mmol) in DMF (3 mL) was added NaH (60% in mineral oil, 90 mg, 2.24 mmol) portionwise. The mixture was stirred at 60° C. for 1.5 h then allowed to cool to RT. The mixture was carefully quenched by pouring into MeOH (10 mL), then 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 0-10% [2M NH3 in MeOH] in DCM, gave the title compound as a brown solid (180 mg, 75%). LCMS (Method 4): Rt 0.49, m/z 378 [MH+].

Workup

  1. temperatureto cool to RT
  2. customThe mixture was carefully quenched
  3. additionby pouring into MeOH (10 mL)
  4. washwashed with MeOH
  5. washThe product was eluted with 2M NH3 in MeOH
  6. concentrationconcentration in vacuo
  7. customgave a residue

Sources & evidence

ORD record
ord-80d41e4de56042b793e04963bc5468a2
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09145413B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes