1-Hydroxybenzotriazole → HCID 74440995, compound

HRID 2098576Notes

Reaction equation

HRID 2098576 reaction equation
[CH:1]1([NH:4][C:5](=[O:24])[C:6]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[CH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.F[P-](F)(F)(F)(F)F.[N:32]1([O:41][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C1C=CC2N(O)N=NC=2C=1.Cl.NO.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH:1]1([NH:4][C:5](=[O:24])[C:6]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[CH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH:32][OH:41])=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 443297Hydroxyamine hydrochlorideHCID 68767501HCID 68767501, compound

Product 1

HCID 74440995HCID 74440995, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-(3-(cyclopropylamino)-2-(p-tolyl)-3-oxoprop-1-en-1-yl)benzoic acid (0.1 g, 0.3 mmol) in DMF (3 mL), benzotriazol-1-yloxy-tris(dimethyl amino)phosphonium hexafluorophosphate (BOP reagent, 0.23 g, 0.55 mmol), HOBt (0.04 g, 0.3 mmol), hydroxylamine hydrochloride (0.03 g, 0.35 mmol), were added followed by DIPEA (0.16 mL, 0.9 mmol). The reaction mixture was stirred for 1 hour, after which the mixture was added to cold water (100 mL) and kept it for 1 hour at 0° C. the white solid formed. The obtained solid was filtered and washed with water (50 mL), dried under vacuum to afford the title compound as white solid (0.080 g, 77% yield). 1H NMR (DMSO-d6) δ (ppm): 0.46-0.51 (2H, m, —CH2), 0.58-0.60 (2H, m, —CH2), 2.29 (3H, s, CH3), 2.69-2.70 (1H, m, —CH), 6.81 (4H, m, Ar—H), 6.97-7.03 (3H, m, Ar—H), 7.36-7.38 (I+1H, d, Ar—H and ═CH), 7.70 (1H, d, NH), 8.99 (1H, s, OH), 11.10 (1H, s, NH), MS m/z: 337.1 (M++1).

Workup

  1. additionwere added
  2. customfor 1 hour
  3. customat 0° C.
  4. customformed
  5. filtrationThe obtained solid was filtered
  6. washwashed with water (50 mL)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-f7b60ec19fa64a3ca44532d7d12dc5e7
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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