HCID 21923045, compound → HCID 178478596, compound

HRID 1272629Notes

Reaction equation

HRID 1272629 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([NH:16][CH2:17][CH2:18][NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=2)[N:3]=1.[NH2:32][C@H:33]1[CH2:38][CH2:37][C@H:36]([NH2:39])[CH2:35][CH2:34]1>>[ClH:1].[ClH:1].[ClH:1].[NH2:32][C@H:33]1[CH2:38][CH2:37][C@H:36]([NH:39][C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][N:8]3[CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[C:4]([NH:16][CH2:17][CH2:18][NH:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([C:28]([F:30])([F:31])[F:29])[CH:22]=3)[N:3]=2)[CH2:35][CH2:34]1

Participants

3

Reactant 2

HCID 21923045HCID 21923045, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178478596HCID 178478596, compoundYield 111.5%

Procedure

The operation is carried out as in Stage 3 of Example 7 starting from 320 mg of the product obtained in Stage 1 above and 770 mg of trans-1,4-diaminocyclohexane and the reaction medium is heated to approximately 140° C. for 3 hours. After purification by chromatography on silica eluting with methylene chloride/methanol/ammonium hydroxide in a proportion of 85/25/1.5 salification is carried out with 1.4N HCl/EtOH, followed by filtering, washing with 5 ml EtOH then drying at ˜50° C. In this way 166 mg of expected product is obtained.

Workup

  1. customAfter purification by chromatography on silica eluting with methylene chloride/methanol/ammonium hydroxide in a proportion of 85/25/1.5 salification
  2. filtrationby filtering
  3. washwashing with 5 ml EtOH
  4. customthen drying at ˜50° C

Sources & evidence

ORD record
ord-42c1d838ad2042588465cb2f761fc90d
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

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