Sodium Iodide → HCID 12094439, compound

HRID 736925Notes

Reaction equation

HRID 736925 reaction equation
[Na+].[I-].C1(OC)C=CC=CC=1.C[Si](Cl)(C)C.[NH2:16][C:17]1[C:47]([C:48]([F:51])([F:50])[F:49])=[CH:46][C:20]([CH2:21][C@H:22]([C:31]([N:33]2[CH2:38][CH2:37][CH:36]([N:39]3[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]3)[CH2:35][CH2:34]2)=[O:32])[CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[CH:19][C:18]=1[Cl:52]>C(#N)C>[NH2:16][C:17]1[C:47]([C:48]([F:50])([F:49])[F:51])=[CH:46][C:20]([CH2:21][C@H:22]([C:31]([N:33]2[CH2:38][CH2:37][CH:36]([N:39]3[CH2:40][CH2:41][N:42]([CH3:45])[CH2:43][CH2:44]3)[CH2:35][CH2:34]2)=[O:32])[CH2:23][C:24]([OH:26])=[O:25])=[CH:19][C:18]=1[Cl:52]

Participants

6

Reactant 4

HCID 5238Sodium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 7519AnisoleHCID 12094440HCID 12094440, compound

Product 1

HCID 12094439HCID 12094439, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

5.75 g (38.4 mmol) of NaI, 3 mL of anisol and 4.92 mL (38.4 mmol) of trimethylsilylchloride were added to the solution of 7.0 g (12.8 mmol) of tert. butyl (S)-3-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-4-oxo-butanoate in 375 mL acetonitrile. The reaction mixture was stirred for 90 min at 40° C., combined with another 5.75 g (38.4 mmol) of NaI and 4.92 mL (38.4 mmol) of trimethylsilylchloride and stirred for a further 2 h at 40° C. The mixture was evaporated down i. vac. and further reacted as the crude product.

Workup

  1. stirringstirred for a further 2 h at 40° C
  2. customThe mixture was evaporated down i
  3. customand further reacted as the crude product

Sources & evidence

ORD record
ord-1ee5782130804b26b606ac7c9dd7e380
Source dataset
uspto-grants-2009_09
Patent number
US07595312B2

Reaction notes

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