1-Hydroxy-2-naphthoic acid → HCID 58865089, compound

HRID 1354830Notes

Reaction equation

HRID 1354830 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([OH:14])=O.C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:48]([O:52][C:53]([NH:55][C@@H:56]1[CH2:61][C@H:60]([NH:62][C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[CH2:59][N:58]([C:70]2[CH:75]=[C:74]([N:76]3[CH2:81][C@@H:80]([NH:82][C:83]([O:85][C:86]([CH3:89])([CH3:88])[CH3:87])=[O:84])[CH2:79][C@@H:78]([NH:90][C:91]([O:93][C:94]([CH3:97])([CH3:96])[CH3:95])=[O:92])[CH2:77]3)[N:73]=[C:72]([NH:98][C:99]3[CH:104]=[CH:103][C:102]([NH2:105])=[CH:101][CH:100]=3)[CH:71]=2)[CH2:57]1)=[O:54])([CH3:51])([CH3:50])[CH3:49]>CC(N(C)C)=O.CCOC(C)=O>[C:48]([O:52][C:53]([NH:55][C@@H:56]1[CH2:61][C@H:60]([NH:62][C:63]([O:65][C:66]([CH3:67])([CH3:68])[CH3:69])=[O:64])[CH2:59][N:58]([C:70]2[CH:75]=[C:74]([N:76]3[CH2:77][C@@H:78]([NH:90][C:91]([O:93][C:94]([CH3:97])([CH3:96])[CH3:95])=[O:92])[CH2:79][C@@H:80]([NH:82][C:83]([O:85][C:86]([CH3:89])([CH3:88])[CH3:87])=[O:84])[CH2:81]3)[N:73]=[C:72]([NH:98][C:99]3[CH:104]=[CH:103][C:102]([NH:105][C:12]([C:3]4[CH:4]=[CH:5][C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[C:2]=4[OH:1])=[O:14])=[CH:101][CH:100]=3)[CH:71]=2)[CH2:57]1)=[O:54])([CH3:49])([CH3:50])[CH3:51]

Participants

7

Reactant 4

HCID 68441-Hydroxy-2-naphthoic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58865616HCID 58865616, compound

Product 1

HCID 58865089HCID 58865089, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

1-Hydroxy-naphthalene-2-carboxylic acid (142) (0.018 g, 0.096 mmol) was dissolved in DMA (2 mL), iPr2EtN (0.096 mmol) was added followed by HBTU (0.036 g, 0.096 mmol) and the mixture was shaken in an 8 mL Teflon septum capped vial at room temperature for 20 minutes. 4,6-bis-((3R,5S)-3,5-bis-(tert-Butoxycarbonylamino)-piperidin-1-yl)-2-(4-aminophenyl-amino)-pyridine (168) (0.055 g, 0.0677 mmol) was added and the mixture was shaken at room temperature for 16 h. LC-MS indicated complete coupling at this point. The mixture was diluted with EtOAc (25 mL) and the organic layer washed with water (15 mL), NaHCO3 (aqueous sat., 15 mL) and brine (15 mL) via extraction, dried over MgSO4 and concentrated to give a brown oil. Purification by flash chromatography on silica gel using a gradient of hexane and EtOAc (eluding with 15–100% EtOAc in hexane for 30 min) gave the desired product (170) as an off-white powder upon concentration (0.042 g, 0.043 mmol, 64% yield). LC-MS (ESI): (exact mass: 981.53) m/e=982.6 [M+H+].

Workup

  1. customcapped vial at room temperature for 20 minutes
  2. washthe organic layer washed with water (15 mL), NaHCO3 (aqueous sat., 15 mL) and brine (15 mL) via extraction
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give a brown oil
  6. customPurification by flash chromatography on silica gel using a gradient of hexane and EtOAc (eluding with 15–100% EtOAc in hexane for 30 min)

Sources & evidence

ORD record
ord-da541be91a4a4f50af9d2f8eb9de84bf
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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