1-Hydroxy-2-naphthoic acid → HCID 58865449, compound

HRID 1354836Notes

Reaction equation

HRID 1354836 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.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.[NH2:48][C:49]1[CH:111]=[CH:110][C:52]([C:53]([NH:55][C:56]2[CH:57]=[C:58]3[C:63](=[CH:64][CH:65]=2)[N:62]=[C:61]([N:66]2[CH2:71][C@@H:70]([NH:72][C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])[CH2:69][C@@H:68]([NH:80][C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])[CH2:67]2)[C:60]([N:88]2[CH2:93][C@@H:92]([NH:94][C:95]([O:97][C:98]([CH3:101])([CH3:100])[CH3:99])=[O:96])[CH2:91][C@@H:90]([NH:102][C:103]([O:105][C:106]([CH3:109])([CH3:108])[CH3:107])=[O:104])[CH2:89]2)=[N:59]3)=[O:54])=[CH:51][CH:50]=1>CN(C=O)C.CCOC(C)=O>[C:76]([O:75][C:73]([NH:72][C@@H:70]1[CH2:69][C@H:68]([NH:80][C:81]([O:83][C:84]([CH3:85])([CH3:86])[CH3:87])=[O:82])[CH2:67][N:66]([C:61]2[C:60]([N:88]3[CH2:93][C@@H:92]([NH:94][C:95]([O:97][C:98]([CH3:101])([CH3:100])[CH3:99])=[O:96])[CH2:91][C@@H:90]([NH:102][C:103]([O:105][C:106]([CH3:108])([CH3:107])[CH3:109])=[O:104])[CH2:89]3)=[N:59][C:58]3[C:63](=[CH:64][CH:65]=[C:56]([NH:55][C:53]([C:52]4[CH:110]=[CH:111][C:49]([NH:48][C:12]([C:3]5[CH:4]=[CH:5][C:6]6[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=6)[C:2]=5[OH:1])=[O:14])=[CH:50][CH:51]=4)=[O:54])[CH:57]=3)[N:62]=2)[CH2:71]1)=[O:74])([CH3:77])([CH3:78])[CH3:79]

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 58865803HCID 58865803, compound

Product 1

HCID 58865449HCID 58865449, compoundYield 12.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Hydroxy-naphthalene-2-carboxylic acid (142) (0.016 g, 0.085 mmol) was dissolved in DMF (0.8 mL) and HBTU (0.032 g, 0.085 mmol) followed by iPr2EtN (0.022 mL, 0.128 mmol) were added. The mixture was shaken at room temperature for 25 minutes. 4-Amino-N-(2,3-bis-((3R,5S)-3,5-bis-(tert-Butoxycarbonylamino)-piperidin-1-yl)-quinoxalin-6-yl)-benzamide (252) (0.06 g, 0.068 mmol) was added and the mixture was shaken at room temperature for 16 h. The mixture was diluted with EtOAc, washed with sodium bicarbonate and brine via extraction, dried over MgSO4 and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of hexane and EtOAc gave the desired product (253) (0.009 g, 0.0085 mmol, 12.5% yield). LC-MS (ESI): (exact mass: 1060.54, mol. wt: 1061.23) m/e=1062.0 [M+1]+.

Workup

  1. additionwere added
  2. stirringthe mixture was shaken at room temperature for 16 h
  3. washwashed with sodium bicarbonate and brine via extraction
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography on silica gel using a gradient of hexane and EtOAc

Sources & evidence

ORD record
ord-d24b2a7fa96f4fee933eedd61e21dce8
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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