Tin tetrachloride → HCID 178500114, compound

HRID 2174111Notes

Reaction equation

HRID 2174111 reaction equation
[C:1]([C:3]1[CH:45]=[CH:44][C:6]2[N:7](COCC[Si](C)(C)C)[C:8]([CH:10]([C:17]3[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH3:28])=[C:22]4[C:18]=3[CH:19]=[CH:20][N:21]4C(OC(C)(C)C)=O)[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:9][C:5]=2[CH:4]=1)#[N:2].C(C1C=CC2N=C(C(C3C(OC)=CC(C)=C4C=3C=CN4C(OC(C)(C)C)=O)CCC(OC)=O)N(COCC[Si](C)(C)C)C=2C=1)#N.[Sn](Cl)(Cl)(Cl)Cl>C(Cl)Cl>[C:1]([C:3]1[CH:45]=[CH:44][C:6]2[NH:7][C:8]([CH:10]([C:17]3[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH3:28])=[C:22]4[C:18]=3[CH:19]=[CH:20][NH:21]4)[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:9][C:5]=2[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 86701753HCID 86701753, compoundHCID 86701754HCID 86701754, compound

Product 1

HCID 178500114HCID 178500114, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution (±)-tert-butyl 4-(1-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-4-methoxy-4-oxobutyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate and (±)-tert-butyl 4-(1-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-4-methoxy-4-oxobutyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 146-A) (0.21 g, 0.332 mmol) in DCM (3.32 ml) was added tin(IV) chloride (3.32 ml, 3.32 mmol) at 0° C. The solution was stirred at 0° C. for 30 minutes and then at room temperature for 1 hour. The reaction was concentrated and absorbed onto silica to purify via FCC (0-50% EtOAc:heptanes) to obtain the title compound. MS (ESI+) m/z 403.4 (M+H).

Workup

  1. waitat room temperature for 1 hour
  2. concentrationThe reaction was concentrated
  3. customabsorbed onto silica
  4. customto purify via FCC (0-50% EtOAc:heptanes)

Sources & evidence

ORD record
ord-2712c22335664d87bee8e62b85bf2ff3
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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