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Triphenylphosphine → HCID 67608484, compound

HRID 1626973
Notes
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Reaction equation

HRID 1626973 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH3:47][O:48][C:49]1[N:54]=[C:53]([CH2:55]O)[CH:52]=[CH:51][CH:50]=1>ClCCl>[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][CH2:55][C:53]1[CH:52]=[CH:51][CH:50]=[C:49]([O:48][CH3:47])[N:54]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 12325389(6-Methoxypyridin-2-yl)methanolHCID 67606759HCID 67606759, compound

Product 1

HCID 67608484HCID 67608484, compound

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

4-Bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-ol (25 mg, 0.093 mmol) and triphenylphosphine (32 mg, 0.12 mmol, 1.3 equiv) were dissolved in dichloromethane (0.5 mL). To the stirring mixture was added diethyl diazene-1,2-dicarboxylate (25 mg, 0.12 mmol, 1.3 equiv), followed by (6-methoxypyridin-2-yl)methanol (16 mg, 0.11 mmol, 1.2 equiv) and the mixture stirred at ambient temperature for 14 hours. The mixture was concentrated in vacuo and the residue was purified by preparative reverse phase HPLC (5: 95 to 95:5; acetonitrile:water containing 0.1% trifluoroacetic acid), providing the title compound as a clear oil: 1H-NMR (400 MHz, d6-DMSO) δ 7.94 (1H, d, J=9.1 Hz), 7.76 (1H, t, J=7.7 Hz), 7.60 (1H, d, J=8.9 Hz), 7.21 (1H, d, J=7.9 Hz), 6.77 (1H, d, J=7.9 Hz), 5.32, (2H, s), 4.59 (2H, d, J=7.31 Hz), 3.84 (3H, s), 1.40-1.32 (1H, m), 0.56-0.53 (2H, m), 0.48-0.44 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 389.0617 [(M+H)+; calculated for C17H17BrN4O2: 389.0607].

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by preparative reverse phase HPLC (5: 95 to 95:5; acetonitrile:water containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-1110cd660ef1488c84029cc660f31e24
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08785481B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes