Potassium Carbonate → benzyl 4-(1-{(S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butyryl}-piperidin-4-yl)-piperazin-1-carboxylate

HRID 736945Notes

Reaction equation

HRID 736945 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[NH:32]1[CH2:37][CH2:36][CH:35]([N:38]2[CH2:43][CH2:42][N:41]([C:44]([O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[O:45])[CH2:40][CH2:39]2)[CH2:34][CH2:33]1.[NH2:54][C:55]1[C:86]([C:87]([F:90])([F:89])[F:88])=[CH:85][C:58]([CH2:59][C@@H:60]([CH2:64][C:65](=[O:84])[N:66]2[CH2:71][CH2:70][CH:69]([N:72]3[CH2:78][CH2:77][C:76]4[CH:79]=[CH:80][CH:81]=[CH:82][C:75]=4[NH:74][C:73]3=[O:83])[CH2:68][CH2:67]2)[C:61](O)=[O:62])=[CH:57][C:56]=1[Cl:91].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:54][C:55]1[C:86]([C:87]([F:89])([F:88])[F:90])=[CH:85][C:58]([CH2:59][C@@H:60]([CH2:64][C:65](=[O:84])[N:66]2[CH2:67][CH2:68][CH:69]([N:72]3[CH2:78][CH2:77][C:76]4[CH:79]=[CH:80][CH:81]=[CH:82][C:75]=4[NH:74][C:73]3=[O:83])[CH2:70][CH2:71]2)[C:61]([N:32]2[CH2:37][CH2:36][CH:35]([N:38]3[CH2:39][CH2:40][N:41]([C:44]([O:46][CH2:47][C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)=[O:45])[CH2:42][CH2:43]3)[CH2:34][CH2:33]2)=[O:62])=[CH:57][C:56]=1[Cl:91]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57470863Benzyl 4-(piperidin-4-yl)piperazine-1-carboxylateHCID 68591515(S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butanoic acid

Product 1

HCID 68591073benzyl 4-(1-{(S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butyryl}-piperidin-4-yl)-piperazin-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

241 mg (0.75 mmol) TBTU, 0.62 mL (3.6 mmol) ethyldiisopropylamine and 215 mg (0.71 mmol) benzyl 4-piperidin-4-yl-piperazin-1-carboxylate were added to a solution of 390 mg (0.71 mmol) (S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butanoic acid in 10 mL DMF and the reaction mixture was stirred overnight at RT. The reaction solution was poured into 80 mL 15% K2CO3 solution, stirred for 10 min at RT, the precipitated substance was suction filtered, washed with 5 mL water and dried in the air over the weekend.

Workup

  1. stirringstirred for 10 min at RT
  2. filtrationfiltered
  3. washwashed with 5 mL water
  4. customdried in the air over the weekend

Sources & evidence

ORD record
ord-9b7ea2a207474fa1a7da846e93cd6527
Source dataset
uspto-grants-2009_09
Patent number
US07595312B2

Reaction notes

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