Triethylamine → HCID 59783610, compound

HRID 1946655Notes

Reaction equation

HRID 1946655 reaction equation
[C:1]1([C:7]2[N:8]([CH2:16][C:17]3[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=3)[C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:27][OH:28].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>N1C=CC=CC=1>[OH:28][NH:27][C:21](=[O:22])[C:20]1[CH:24]=[CH:25][C:17]([CH2:16][N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:15]=[C:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 443297Hydroxyamine hydrochlorideHCID 59783766HCID 59783766, compound

Product 1

HCID 59783610HCID 59783610, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Title compound 496 (332 mg, 1.014 mmol), hydroxylamine hydrochloride (85 mg, 1.217 mmol), BOP (583 mg, 1.318 mmol), triethylamine (0.424 mL, 3.04 mmol) and pyridine (7 mL) were stirred together at room temperature for 1 hour. All solvents were then removed under reduced pressure, and the residue was diluted with ethyl acetate and brine. Following extraction with ethyl acetate, the combined organic layers were dried with anhydrous sodium sulfate, filtered, and concentrated. The residue was then purified by column chromatography on silica gel using 50-100% EtOAc/hexanes as the eluent to afford title compound 497 (0.058 g, 17%) as a white solid. 1H NMR (CD3OD) δ (ppm): 7.66-7.62 (m, 3H), 7.50-7.38 (m, 5H), 7.28-7.23 (m, 1H), 7.17-7.08 (m, 2H), 7.03 (d, J=8.4 Hz, 2H), 6.65 (d, J=0.6 Hz, 1H), 5.51 (s, 2H). MS (m/z): 343.5 (M+H).

Workup

  1. customAll solvents were then removed under reduced pressure
  2. additionthe residue was diluted with ethyl acetate and brine
  3. extractionextraction with ethyl acetate
  4. dry with materialthe combined organic layers were dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was then purified by column chromatography on silica gel using 50-100% EtOAc/hexanes as the eluent

Sources & evidence

ORD record
ord-c6145b0953bc47bf826ed4df65e6321d
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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