Potassium Carbonate → HCID 57807391, compound

HRID 2106559Notes

Reaction equation

HRID 2106559 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:33][C:34]3[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[C:37]([NH2:44])=[C:36]([Cl:45])[CH:35]=3)[C:19](=[O:32])[N:20]3[CH2:25][CH2:24][N:23]([CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[CH2:22][CH2:21]3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:46]=[CH:47][CH:48]=[CH:49][C:4]=2[NH:3]1.C([O-])([O-])=O.[K+].[K+].Br[C:57]([CH3:64])([CH3:63])[C:58]([O:60][CH2:61][CH3:62])=[O:59]>CN(C=O)C>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:33][C:34]3[CH:39]=[C:38]([C:40]([F:41])([F:43])[F:42])[C:37]([NH2:44])=[C:36]([Cl:45])[CH:35]=3)[C:19]([N:20]3[CH2:21][CH2:22][N:23]([CH:26]4[CH2:31][CH2:30][N:29]([C:57]([C:58]([O:60][CH2:61][CH3:62])=[O:59])([CH3:64])[CH3:63])[CH2:28][CH2:27]4)[CH2:24][CH2:25]3)=[O:32])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:46]=[CH:47][CH:48]=[CH:49][C:4]=2[NH:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 57848474HCID 57848474, compound

Product 1

HCID 57807391HCID 57807391, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 140 mg (0.20 mmol) (R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-oxo-2-(4-piperidin-4-yl-piperazin-1-yl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate (Example 29a), 60.8 mg (0.44 mmol) K2CO3 and 45 μL (0.30 mmol) ethyl 2-bromo-2-methyl-propionate in 1.8 mL DMF was shaken at 50° C. for 12 h and then for 48 h at RT. The precipitate was filtered off and the filtrate was purified by HPLC without working up; the fractions containing the product were combined, evaporated down i. vac., the residue was made alkaline with saturated NaHCO3 solution, the precipitate was suction filtered, washed with 20 mL water and dried at 40° C.

Workup

  1. waitfor 48 h at RT
  2. filtrationThe precipitate was filtered off
  3. customthe filtrate was purified by HPLC
  4. additionthe fractions containing the product
  5. customevaporated down i
  6. filtrationfiltered
  7. washwashed with 20 mL water
  8. customdried at 40° C.

Sources & evidence

ORD record
ord-faa04970992b462d8fa889fb24142754
Source dataset
uspto-grants-2009_08
Patent number
US07579341B2

Reaction notes

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