Sodium Iodide → HCID 131721977, compound

HRID 1953065Notes

Reaction equation

HRID 1953065 reaction equation
[Cl:1][C:2]1[N:8]([CH2:9][CH2:10][CH2:11][CH2:12]Cl)[C:7](=[O:14])[C:6]2[CH:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:5]=2[O:4][CH:3]=1.N1C=CC=NC=1[N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.[I-].[Na+].C([N:36]([CH2:39][CH3:40])[CH2:37]C)C.[CH3:41][N:42](C)C=O>>[Cl:1][C:2]1[N:8]([CH2:9][CH2:10][CH2:11][CH2:12][N:26]2[CH2:27][CH2:28][CH:29]([C:37]3[N:36]=[CH:39][CH:40]=[CH:41][N:42]=3)[CH2:30][CH2:31]2)[C:7](=[O:14])[C:6]2[CH:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:5]=2[O:4][CH:3]=1

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 8471TriethylamineHCID 114465182-(Piperidin-1-yl)pyrimidineHCID 18328146HCID 18328146, compound

Product 1

HCID 131721977HCID 131721977, compoundYield 83%

Procedure

129 mg of the 3-chloro-4-(4-chlorobutyl)-4,5-dihydro-7-methyl-1,4-benzoxazepin-5-one synthesized by the method of Example 19 described in International Publication WO96/24594 was dissolved in 2 ml of dimethylformamide, then 106 mg (1.5 equivalents) of 1-(2-pyrimidinyl)piperadine, 129 mg (2 equivalents) of sodium iodide, and 87 mg (2 equivalents) of triethylamine were added and the resultant mixture agitated at 90° C. for 7 hours. This was then treated and purified in the same way as Example 13 to obtain 152 mg of the above-referenced compound (yield 83%). Note that the dichloride was obtained by making a dichloride by an ordinary method, then recrystallizing from ether.

Workup

  1. additionThis was then treated
  2. custompurified in the same way as Example 13

Sources & evidence

ORD record
ord-d856a144f3a340ed861e81022b6ae944
Source dataset
uspto-grants-2000_09
Patent number
US06114522

Reaction notes

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