Methanol → HCID 58204363, compound

HRID 1498445Notes

Reaction equation

HRID 1498445 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)[N:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[NH:24]1[CH2:29][CH2:28][CH:27]([CH2:30][OH:31])[CH2:26][CH2:25]1.CO>C(Cl)Cl>[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[C:16]4[CH:19]=[N:20][C:21]([N:24]5[CH2:29][CH2:28][CH:27]([CH2:30][OH:31])[CH2:26][CH2:25]5)=[CH:22][C:15]=4[O:14][CH2:13][CH2:12][N:11]3[CH:10]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 4207714-PiperidinemethanolHCID 1360309132-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-ol

Product 1

HCID 58204363HCID 58204363, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedures of Example 339, 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-ol from Example 93 and 4-piperidine methanol, were reacted and the crude product subjected to flash chromatography (SiO2, gradient 0 to 8% methanol in DCM) then recrystallisation from methanol to give 372 as a white solid (69 mg, 48%). LCMS: RT=2.57 min, [M+H]+=410. 1H NMR 400 MHz (DMSO-d6) δ: 9.10 (1 H, s), 7.90 (1 H, s), 7.84 (1 H, s), 6.32 (1 H, s), 5.99-5.90 (1 H, m), 4.54-4.44 (5 H, m), 4.34 (2 H, d, J=13.11 Hz), 3.28 (2 H, t, J=5.64 Hz), 2.84 (2 H, t, J=12.55 Hz), 1.71 (2 H, d, J=13.74 Hz), 1.65 (1 H, m), 1.49 (6 H, d, J=6.60 Hz), 1.13 (2 H, t, J=12.33 Hz)

Workup

  1. customwere reacted
  2. customrecrystallisation from methanol

Sources & evidence

ORD record
ord-49f2f0ded0ba4d998000205abe710ac8
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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