Potassium Carbonate → (S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-1-(4-dimethylamino-piperidin-1-yl)-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butan-1,4-dione

HRID 736942Notes

Reaction equation

HRID 736942 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.[CH3:32][N:33]([CH3:40])[CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.[NH2:41][C:42]1[C:73]([C:74]([F:77])([F:76])[F:75])=[CH:72][C:45]([CH2:46][C@@H:47]([CH2:51][C:52](=[O:71])[N:53]2[CH2:58][CH2:57][CH:56]([N:59]3[CH2:65][CH2:64][C:63]4[CH:66]=[CH:67][CH:68]=[CH:69][C:62]=4[NH:61][C:60]3=[O:70])[CH2:55][CH2:54]2)[C:48](O)=[O:49])=[CH:44][C:43]=1[Cl:78].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:41][C:42]1[C:73]([C:74]([F:76])([F:75])[F:77])=[CH:72][C:45]([CH2:46][C@@H:47]([CH2:51][C:52]([N:53]2[CH2:58][CH2:57][CH:56]([N:59]3[CH2:65][CH2:64][C:63]4[CH:66]=[CH:67][CH:68]=[CH:69][C:62]=4[NH:61][C:60]3=[O:70])[CH2:55][CH2:54]2)=[O:71])[C:48]([N:37]2[CH2:38][CH2:39][CH:34]([N:33]([CH3:40])[CH3:32])[CH2:35][CH2:36]2)=[O:49])=[CH:44][C:43]=1[Cl:78]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 417391N,N-Dimethylpiperidin-4-amineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 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 57848212(S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-1-(4-dimethylamino-piperidin-1-yl)-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butan-1,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

80.3 mg (0.25 mmol) TBTU, 0.21 mL (1.2 mmol) ethyldiisopropylamine and 38.5 mg (0.3 mmol) dimethyl-piperidin-4-yl-amine were added to a solution of 130 mg (0.24 mmol) (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 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. Then the product was purified by chromatography using HPLC.

Workup

  1. stirringstirred for 10 min at RT
  2. filtrationfiltered
  3. washwashed with 5 mL water
  4. customdried in the air over the weekend
  5. customThen the product was purified by chromatography

Sources & evidence

ORD record
ord-4ed3dbde9fc544ffa4d97abd5cb99b99
Source dataset
uspto-grants-2009_09
Patent number
US07595312B2

Reaction notes

Loading…