[3-(8-Isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydro-pteridin-2-ylamino)-5-(methylsulfonyl)-phenyl]-thiocarbamic acid ethyl ester → (4-[3-[3-(8-Isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydro-pteridin-2-ylamino)-5-(methylsulfonyl)-phenyl]-ureido]-cyclohexyl)-carbamic acid tert butyl ester

HRID 1958006Notes

Reaction equation

HRID 1958006 reaction equation
C([O:3][C:4](=S)[NH:5][C:6]1[CH:11]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:9]=[C:8]([NH:16][C:17]2[N:26]=[CH:25][C:24]3[N:23]([CH3:27])[C:22](=[O:28])[CH2:21][N:20]([CH:29]([CH3:31])[CH3:30])[C:19]=3[N:18]=2)[CH:7]=1)C.[C:33]([O:37][C:38](=[O:47])[NH:39][C@H:40]1[CH2:45][CH2:44][C@@H:43]([NH2:46])[CH2:42][CH2:41]1)([CH3:36])([CH3:35])[CH3:34]>CN(C=O)C.O>[C:33]([O:37][C:38](=[O:47])[NH:39][CH:40]1[CH2:41][CH2:42][CH:43]([NH:46][C:4]([NH:5][C:6]2[CH:11]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:9]=[C:8]([NH:16][C:17]3[N:26]=[CH:25][C:24]4[N:23]([CH3:27])[C:22](=[O:28])[CH2:21][N:20]([CH:29]([CH3:31])[CH3:30])[C:19]=4[N:18]=3)[CH:7]=2)=[O:3])[CH2:44][CH2:45]1)([CH3:36])([CH3:34])[CH3:35]

Participants

5

Reactant 2

HCID 86640955[3-(8-Isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydro-pteridin-2-ylamino)-5-(methylsulfonyl)-phenyl]-thiocarbamic acid ethyl esterHCID 178418966HCID 178418966, compound

Product 1

HCID 59286116(4-[3-[3-(8-Isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydro-pteridin-2-ylamino)-5-(methylsulfonyl)-phenyl]-ureido]-cyclohexyl)-carbamic acid tert butyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

[3-(8-Isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydro-pteridin-2-ylamino)-5-(methylsulfonyl)-phenyl]-thiocarbamic acid ethyl ester (150 mg; 0.313 mmol) was dissolved in 1 ml of dry DMF, tert-butyl-cis-4-aminocyclohexylcarbamate (201 mg; 0.940 mmol) was added. The reaction mixture was stirred at 70° C., overnight, then, it was diluted with water. The precipitated formed was filtered, washed with water and dried in vacuo. 196 mg (0.311 mmol; 99% yield) of the desired compound to were obtained.

Workup

  1. customThe precipitated formed
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-33fe0f9135d941abaf997dd0bbc8a9c4
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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