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1-Hydroxybenzotriazole → HCID 10054950, compound

HRID 644308
Notes
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Reaction equation

HRID 644308 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][N:37]([CH: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][CH:40]([N:37]2[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]2)[CH2:41][CH2:42]1)=[O:59])[CH3:47]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 7957071-Methyl-4-(piperidin-4-yl)piperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68579989HCID 68579989, compound

Product 1

HCID 10054950HCID 10054950, compound

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

336 mg (1.05 mmol) of TBTU, 161 mg (1.05 mmol) of HOBt, 0.75 mL of triethylamine and 192 mg (1.05 mmol) of 1-methyl-4-piperidin-4-yl-piperazine 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, and stirred for 4 h at RT and 2 h at 40° C. The solvent was removed in vacuo, the residue taken up in 40 mL of saturated NaHCO3 solution, exhaustively extracted with EtOAc and dried over MgSO4. After elimination of the desiccant and solvent the crude product was purified by chromatography (silica gel, MeOH/NH3 100:3).

Workup

  1. customThe solvent was removed in vacuo
  2. extractionexhaustively extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. customAfter elimination of the desiccant and solvent the crude product was purified by chromatography (silica gel, MeOH/NH3 100:3)

Sources & evidence

ORD record
ord-480f72a7108f44dcb7c794b21541b3b2
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07700589B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes