1-Hydroxybenzotriazole → HCID 59260987, compound

HRID 644309Notes

Reaction equation

HRID 644309 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[CH3:33][N:34]1[CH2:39][CH2:38][CH:37]([N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH2:36][CH2:35]1.[CH2:46]([C:48]1[CH:49]=[C:50]([CH2:56][CH:57]([NH:61][C:62]([N:64]2[CH2:69][CH2:68][CH:67]([N:70]3[CH2:79][C:78]4[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=4)[NH:72][C:71]3=[O:80])[CH2:66][CH2:65]2)=[O:63])[C:58](O)=[O:59])[CH:51]=[CH:52][C:53]=1[CH2:54][CH3:55])[CH3:47]>C1COCC1.C(N(CC)CC)C>[CH2:46]([C:48]1[CH:49]=[C:50]([CH:51]=[CH:52][C:53]=1[CH2:54][CH3:55])[CH2:56][CH:57]([NH:61][C:62]([N:64]1[CH2:69][CH2:68][CH:67]([N:70]2[CH2:79][C:78]3[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=3)[NH:72][C:71]2=[O:80])[CH2:66][CH2:65]1)=[O:63])[C:58]([N:43]1[CH2:44][CH2:45][N:40]([CH:37]2[CH2:36][CH2:35][N:34]([CH3:33])[CH2:39][CH2:38]2)[CH2:41][CH2:42]1)=[O:59])[CH3:47]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68579989HCID 68579989, compound

Product 1

HCID 59260987HCID 59260987, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

336 mg (1.05 mmol) of TBTU, 161 mg (1.05 mmol) of HOBt, 1.02 mL triethylamine and 326 mg (1.05 mmol) of 1-(1-methyl-piperidin-4-yl)-piperazine (used as the tris-hydrochloride) were added to a solution of 500 mg (1.05 mmol) of 3-(3,4-diethyl-phenyl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid in 100 mL of THF, stirred for 4 h at RT and 2 h at 40° C. The solvent was removed in vacuo, the residue was stirred with 40 mL of saturated NaHCO3 solution, the precipitated product was suction filtered, taken up in MeOH and purified by chromatography over silica gel (MeOH). The product fractions were evaporated down, the residue triturated with diethyl ether, suction filtered, washed twice with diethyl ether and dried.

Workup

  1. customThe solvent was removed in vacuo
  2. stirringthe residue was stirred with 40 mL of saturated NaHCO3 solution
  3. filtrationfiltered
  4. custompurified by chromatography over silica gel (MeOH)
  5. customThe product fractions were evaporated down
  6. customthe residue triturated with diethyl ether, suction
  7. filtrationfiltered
  8. washwashed twice with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-78534e91aa684edba3880e1467f0f600
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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