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3-Pyrroline → HCID 178521018, compound

HRID 931315
Notes
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Reaction equation

HRID 931315 reaction equation
[NH:1]1[CH2:5][CH:4]=[CH:3][CH2:2]1.[Cl:6][C:7]1[CH:8]=[N:9][N:10]([C:12]2([C:15]3[NH:32][C:18]4=[N:19][C:20]([N:23]5[CH2:28][CH2:27][CH2:26][C@@H:25]([C:29](O)=[O:30])[CH2:24]5)=[CH:21][CH:22]=[C:17]4[N:16]=3)[CH2:14][CH2:13]2)[CH:11]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>ClCCl>[Cl:6][C:7]1[CH:8]=[N:9][N:10]([C:12]2([C:15]3[NH:32][C:18]4=[N:19][C:20]([N:23]5[CH2:28][CH2:27][CH2:26][C@@H:25]([C:29]([N:1]6[CH2:5][CH:4]=[CH:3][CH2:2]6)=[O:30])[CH2:24]5)=[CH:21][CH:22]=[C:17]4[N:16]=3)[CH2:14][CH2:13]2)[CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 660593-PyrrolineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178525787HCID 178525787, compound

Product 1

HCID 178521018HCID 178521018, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Pyrroline (98.5 mg, 1.41 mmol) was added to a solution of (R)-1-(2-(1-(4-chloro-1H-pyrazol-1-yl)cyclopropyl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylic acid (500 mg, 1.29 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′,-tetramethyluronium hexafluorophosphate (HATU) (541 mg, 1.41 mmol) and diisopropylethylamine (334.7 mg, 2.58 mmol) in anhydrous dichloromethane (20 mL). The reaction mixture was stirred at room temperature for 2 h. The mixture was partitioned between dichloromethane and water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude material was triturated with pentane to afford the title compound (510 mg). MS (ES+) (M+H) 438.0; LCMS retention time 4.935 min (Method R1).

Workup

  1. customThe mixture was partitioned between dichloromethane and water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was triturated with pentane

Sources & evidence

ORD record
ord-733c2ace24d04d0f8bf79a2276aa8299
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296745B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes