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Triphenylphosphine → HCID 68312705, compound

HRID 1530370
Notes
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Reaction equation

HRID 1530370 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]([OH:23])[CH:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][C:6]([CH3:24])=[N:5]1)([CH3:3])[CH3:2].[CH2:25]([O:32][C:33]([N:35]1[CH2:40][CH2:39][CH:38]([CH:41](O)[CH2:42][CH3:43])[CH2:37][CH2:36]1)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCOCC1.CCOC(C)=O>[CH2:25]([O:32][C:33]([N:35]1[CH2:40][CH2:39][CH:38]([CH:41]([O:23][C:21]2[CH:20]=[CH:19][C:16]3[C:17]4[N:11]([CH2:12][CH2:13][O:14][C:15]=3[CH:22]=2)[CH:10]=[C:9]([C:8]2[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[C:6]([CH3:24])[N:7]=2)[N:18]=4)[CH2:42][CH3:43])[CH2:37][CH2:36]1)=[O:34])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 68313085HCID 68313085, compoundHCID 136414067HCID 136414067, compound

Product 1

HCID 68312705HCID 68312705, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 8857
Ethyl Acetate
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-ol (300 mg, 0.92 mmol), 4-(1-hydroxypropyl)piperidine-1-carboxylic acid benzyl ester (308 mg, 1.11 mmol) and triphenylphosphine (411 mg, 1.38 mmol) in dioxane (5 mL) was added dropwise DEAD (217 ul, 1.38 mmol) and the reaction mixture was stirred at RT for 4 h. The mixture was then diluted with EtOAc and washed with NaOH aq. (1N). The organic phase was washed with brine, then dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-10% MeOH in EtOAc) affording 4-{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]propyl}piperidine-1-carboxylic acid benzylester (280 mg, 51%). 1H NMR (CDCl3, 400 MHz): δ 8.40 (1H, d, J=8.97 Hz), 7.59 (1H, s), 7.37-7.28 (5H, m), 6.73 (1H, dd, J=8.99, 2.56 Hz), 6.54 (1H, d, J=2.52 Hz), 5.98-5.87 (1H, m), 5.14 (2H, s), 4.51-4.45 (2H, m), 4.44-4.37 (2H, m), 4.34-4.19 (2H, bs), 4.09-4.03 (1H, m), 2.83-2.68 (2H, m), 2.43 (3H, s), 1.88-1.78 (1H, m), 1.75-1.61 (5H, m), 1.58 (6H, d, J=6.65 Hz), 1.38-1.30 (1H, m), 0.97 (3H, t, J=7.37 Hz).

Workup

  1. washwashed with NaOH aq. (1N)
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 0-10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-473662020cc141f6984e5aa1d55aebea
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09090628B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes