Acetic Acid → HCID 16071177, compound

HRID 2267235Notes

Reaction equation

HRID 2267235 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.CC(O)=O.[O:16]=[C:17]1[N:23]([CH:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C@H:33]([CH2:43][C:44]3[CH:49]=[C:48]([C:50]([F:53])([F:52])[F:51])[C:47]([NH2:54])=[C:46]([Cl:55])[CH:45]=3)[C:34](=[O:42])[N:35]3[CH2:40][CH2:39][C:38](=O)[CH2:37][CH2:36]3)=[O:31])[CH2:26][CH2:25]2)[CH2:22][CH2:21][C:20]2[CH:56]=[CH:57][CH:58]=[CH:59][C:19]=2[NH:18]1.[BH3-]C#N.[Na+]>C1COCC1.CO>[NH2:54][C:47]1[C:48]([C:50]([F:52])([F:53])[F:51])=[CH:49][C:44]([CH2:43][C@@H:33]([O:32][C:30]([N:27]2[CH2:28][CH2:29][CH:24]([N:23]3[CH2:22][CH2:21][C:20]4[CH:56]=[CH:57][CH:58]=[CH:59][C:19]=4[NH:18][C:17]3=[O:16])[CH2:25][CH2:26]2)=[O:31])[C:34]([N:35]2[CH2:36][CH2:37][CH:38]([N:1]3[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]3)[CH2:39][CH2:40]2)=[O:42])=[CH:45][C:46]=1[Cl:55]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 70770Ethyl 4-piperidinecarboxylateHCID 5003444Sodium cyanoborohydrideHCID 66941865HCID 66941865, compound

Product 1

HCID 16071177HCID 16071177, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

62.9 mg (0.4 mmol) ethyl piperidine-4-carboxylate and 11 μL (0.2 mmol) AcOH were added to a solution of 127 mg (0.2 mmol) (R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-oxo-2-(4-oxo-piperidin-1-yl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate in 2 mL THF/MeOH (2:1) and the reaction mixture was stirred for 2 h at RT. Then it was cooled to 0° C., combined with 10.6 mg (0.16 mmol) NaBH3CN after 2 h and stirred at 0° C. overnight. The solvent was allowed to evaporate, the residue was taken up in 2 mL DMF and the crude product was purified by HPLC. The fractions containing the product were combined and freeze-dried.

Workup

  1. temperatureThen it was cooled to 0° C.
  2. stirringstirred at 0° C. overnight
  3. customto evaporate
  4. customthe crude product was purified by HPLC
  5. additionThe fractions containing the product
  6. customfreeze-dried

Sources & evidence

ORD record
ord-4b77b00032af4804b422409f23bc1fa4
Source dataset
uspto-grants-2010_12
Patent number
US07858622B2

Reaction notes

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