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1-Hydroxybenzotriazole → 4-(2-Oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid-[1-(3,4-diethyl-benzyl)-2-(1'-methyl-4,4'-bipiperidinyl-1-yl)-2-oxo-ethyl]-amide

HRID 644302
Notes
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Reaction equation

HRID 644302 reaction equation
CN(C(ON1N=[N:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]1=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]([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[CH2:76][CH2:75]C4C=CC=CC=4N[C:71]3=[O:81])[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[CH2:76][CH2:75][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[NH:16][C:71]2=[O:81])[CH2:66][CH2:65]1)=[O:63])[C:58]([N:43]1[CH2:44][CH2:45][CH: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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 71830411-Methyl-4,4'-bipiperidineHCID 221845783-(3,4-Diethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid

Product 1

HCID 10439299
4-(2-Oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid-[1-(3,4-diethyl-benzyl)-2-(1'-methyl-4,4'-bipiperidinyl-1-yl)-2-oxo-ethyl]-amide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

0.3 mL of triethylamine, 323 mg (1.01 mmol) of TBTU, 155 mg (1.01 mmol) of HOBt and 184 mg (1.01 mmol) of methyl-[4,4′]bipiperidinyl were added to a solution of 500 mg (1.02 mmol) of 3-(3,4-diethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid in 50 mL of THF and stirred for 4 h at RT and 2 h at 40° C. The reaction mixture was evaporated down, the residue was stirred with 40 mL of saturated NaHCO3 solution, the precipitated product was suction filtered, washed twice with water and triturated with EtOH. The white substance precipitated was suction filtered and washed twice with diethyl ether.

Workup

  1. customThe reaction mixture was evaporated down
  2. stirringthe residue was stirred with 40 mL of saturated NaHCO3 solution
  3. filtrationfiltered
  4. washwashed twice with water
  5. customtriturated with EtOH
  6. customThe white substance precipitated
  7. filtrationfiltered
  8. washwashed twice with diethyl ether

Sources & evidence

ORD record
ord-4ba66bfae60f48fd8cbe0ddd142c6f43
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