1-Methylpiperazine → HCID 68312918, compound

HRID 1530436Notes

Reaction equation

HRID 1530436 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[N:11]([CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([O:23][C:24]5([C:27](O)=[O:28])[CH2:26][CH2:25]5)[CH:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][C:6]([CH3:30])=[N:5]1)([CH3:3])[CH3:2].[CH3:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[N:11]([CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([O:23][C:24]5([C:27]([N:35]6[CH2:36][CH2:37][N:32]([CH3:31])[CH2:33][CH2:34]6)=[O:28])[CH2:25][CH2:26]5)[CH:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][C:6]([CH3:30])=[N:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68312953HCID 68312953, compound

Product 1

HCID 68312918HCID 68312918, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]cyclopropanecarboxylic acid (90 mg, 0.22 mmol), 1-methylpiperazine (29 uL, 0.26 mmol), HATU (108 mg, 0.29 mmol) and DIPEA (52 uL, 0.31 mmol) in DMF (3 mL) was stirred at RT for 2 h. Volatiles were removed under reduced pressure and the resulting residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with water, followed by brine, then dried (MgSO4) and concentrated in vacuo affording {1-[2-(2-Isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]cyclopropyl}-(4-methylpiperazin-1-yl)methanone (quantitative). LCMS: RT 2.08 min [M+H]+ 492.2

Workup

  1. customVolatiles were removed under reduced pressure
  2. customthe resulting residue was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organic layers were washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c3db574988584f65a2e1900685817fa1
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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