Water → HCID 25003478, compound

HRID 1015360Notes

Reaction equation

HRID 1015360 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][O:13][C:14]2[CH:21]=[CH:20][CH:19]=[C:18](F)[C:15]=2[C:16]#[N:17])[CH2:8][CH2:7]1.C(=O)(O)O.[NH2:30][C:31]([NH2:33])=[NH:32].O>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][O:13][C:14]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:15]=2[C:16]([NH2:17])=[N:32][C:31]([NH2:33])=[N:30]3)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 286947Carbonic acid-guanidine (1:1)HCID 67301339HCID 67301339, compound

Product 1

HCID 25003478HCID 25003478, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2-[4-(3-Chlorobenzyl)cyclohexylmethoxy]-6-fluorobenzonitrile (150 mg; 0.42 mmol) was heated to 135° C. in the presence of guanidine carbonate (76 mg; 0.42 mmol) in 1.5 mLs of dimethylacetamide. After 6 hours, mixture was cooled to room temperature and 2 mLs of water added. After 30 minutes solids were collected by filtration. Solids were purified by trituration using a 3:1 mixture of ethyl alcohol and water. Solids collected by filtration to give title compound as a white solid. (128 mgs; 76% yield).

Workup

  1. filtrationAfter 30 minutes solids were collected by filtration
  2. customSolids were purified by trituration
  3. additiona 3:1 mixture of ethyl alcohol and water
  4. filtrationSolids collected by filtration

Sources & evidence

ORD record
ord-48a5dad2c6ca47019c31f4be2eb8c70d
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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