Azetidine → HCID 178521017, compound

HRID 931299Notes

Reaction equation

HRID 931299 reaction equation
[NH:1]1[CH2:4][CH2:3][CH2:2]1.[Cl:5][C:6]1[CH:7]=[N:8][N:9]([C:11]2([C:14]3[NH:31][C:17]4=[N:18][C:19]([N:22]5[CH2:27][CH2:26][CH2:25][C@@H:24]([C:28](O)=[O:29])[CH2:23]5)=[CH:20][CH:21]=[C:16]4[N:15]=3)[CH2:13][CH2:12]2)[CH:10]=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>[N:1]1([C:28]([C@@H:24]2[CH2:25][CH2:26][CH2:27][N:22]([C:19]3[N:18]=[C:17]4[NH:31][C:14]([C:11]5([N:9]6[CH:10]=[C:6]([Cl:5])[CH:7]=[N:8]6)[CH2:12][CH2:13]5)=[N:15][C:16]4=[CH:21][CH:20]=3)[CH2:23]2)=[O:29])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 10422AzetidineHCID 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 178521017HCID 178521017, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Azetidine (0.1 mL, 1.42 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 (50 mg, 1.29 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′,-tetramethyluronium hexafluorophosphate (HATU) (49 mg, 1.29 mmol) and diisopropylethylamine (0.1 mL, 3.88 mmol) in anhydrous dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 2 h, then was partitioned between dichloromethane and water. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via preparative TLC to afford the title compound (35 mg). MS (ES+APCI) (M+H) 426.1; LCMS retention time: 3.440 min (Method S1).

Workup

  1. customwas partitioned between dichloromethane and water
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified via preparative TLC

Sources & evidence

ORD record
ord-37cd642fc9f0414e80068ef78801cf2c
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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