Chloroform → HCID 21309650, compound

HRID 617293Notes

Reaction equation

HRID 617293 reaction equation
[C:1]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[N:15]=[N:16][CH:17]=[CH:18][C:19]=1Cl)(OC(C)(C)C)=O.[NH4+].[OH-].C(Cl)(Cl)[Cl:24]>CO>[Cl:24][C:17]1[N:16]=[N:15][C:14]([O:13][CH2:12][C@@H:9]2[CH2:10][CH2:11][N:8]2[CH3:1])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6212Chloroform2×HCID 14923Ammonium HydroxideHCID 18391698HCID 18391698, compound

Product 1

HCID 21309650HCID 21309650, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The compound from step 13a (805 mg, 2.68 mmol) was treated in a similar fashion as that described under Example 7d. The crude was subject to flash chromatography on silica gel with 10% MeOH in CHCl3 to 0.5% NH4OH in 10% MeOH in CHCl3 used as the elutant to give 352 mg of a yellow oil (66% yield). MS (CI) m/e 200 (M+H)+. The amine deprotected material (330 mg, 1.66 mmol) was then subjected to reductive amination conditions previously described in Example 8. The crude product was purified by flash chromatography on silica gel using 2% MeOH in CHCl3 to 5% MeOH in CHCl3 as the elutant to give 125 mg of a clear oil (35% yield). MS (CI) m/e 214 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 7.36 (d, J=9.2 Hz, 1H), 7.02 (d, J=9.2 Hz, 1H, 4.54 (dd, J=11.6 Hz, 3.8 Hz, 1H), 4.47 (dd, J=11.6 Hz, 5.7 Hz, 1H, 3.48-3.39 (m, 2H), 2.89-2.81 (m, 1H), 2.38 (s, 3H), 2.17-2.03 (m, 2H).

Sources & evidence

ORD record
ord-1f38e052e69c4abdb0297db482ad7bc9
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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