Triethylamine → HCID 68608407, compound

HRID 642815Notes

Reaction equation

HRID 642815 reaction equation
[C:1]([C@H:4]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([N:32]2[CH2:38][CH2:37][C:36]3[CH:39]=[CH:40][CH:41]=[CH:42][C:35]=3[NH:34][C:33]2=[O:43])[CH2:28][CH2:27]1)=[O:25])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([CH3:15])[CH:14]=1)[N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[N:10]=[CH:9]2)(O)=[O:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[CH3:73][N:74]1[CH2:79][CH2:78][N:77]([CH:80]2[CH2:85][CH2:84][NH:83][CH2:82][CH2:81]2)[CH2:76][CH2:75]1>CN(C=O)C>[CH3:15][C:13]1[CH:14]=[C:6]([CH2:5][C@@H:4]([O:23][C:24]([N:26]2[CH2:27][CH2:28][CH:29]([N:32]3[CH2:38][CH2:37][C:36]4[CH:39]=[CH:40][CH:41]=[CH:42][C:35]=4[NH:34][C:33]3=[O:43])[CH2:30][CH2:31]2)=[O:25])[C:1]([N:83]2[CH2:82][CH2:81][CH:80]([N:77]3[CH2:76][CH2:75][N:74]([CH3:73])[CH2:79][CH2:78]3)[CH2:85][CH2:84]2)=[O:2])[CH:7]=[C:8]2[C:12]=1[N:11]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[N:10]=[CH:9]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 7957071-Methyl-4-(piperidin-4-yl)piperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68609264HCID 68609264, compound

Product 1

HCID 68608407HCID 68608407, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 440 mg tert.-butyl 5-{(R)-2-carboxy-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-ethyl}-7-methyl-indazol-1-carboxylate, 256 mg (0.8 mmol) TBTU, 146 μL (1.0 mmol) triethylamine and 147 mg (0.8 mmol) 1-methyl-4-piperidin-4-yl-piperazine in 8 mL DMF was stirred for 2 h at RT. The reaction solution was filtered through an injection filter and purified directly by HPLC without any further working up. The fractions containing the product were combined, evaporated down i.vac., made alkaline with 15% K2CO3 solution, extracted three times with 30 mL DCM, the combined organic phases were dried over Na2SO4 and the solvent was eliminated i. vac.

Workup

  1. filtrationThe reaction solution was filtered through an injection
  2. filtrationfilter
  3. custompurified directly by HPLC without
  4. additionThe fractions containing the product
  5. customevaporated down i.vac
  6. extractionextracted three times with 30 mL DCM
  7. dry with materialthe combined organic phases were dried over Na2SO4

Sources & evidence

ORD record
ord-ab7c04623b6f4144b8ef3ef8f21dbeae
Source dataset
uspto-grants-2010_04
Patent number
US07696195B2

Reaction notes

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