1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59312929, compound

HRID 2389758Notes

Reaction equation

HRID 2389758 reaction equation
Cl[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[N:3]=1.[SH:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].N12CCCN=C1CCCCC2>>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[C:4]1[N:3]=[C:2]([S:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=1

Participants

4

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 3017761N-(tert-butoxycarbonyl)-2-aminoethanethiolHCID 59312932HCID 59312932, compound

Product 1

HCID 59312929HCID 59312929, compound

Procedure

tert-Butyl (2-{[7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]thio}ethyl)carbamate (Example 44A) is synthesized in analogy to the preparation of Example 42A from 5-chloro-7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidine (Example 6A) (500 mg, 17 mmol), tert-butyl (2-mercaptoethyl)carbamate (445 mg, 2.5 mmol) and 1,8-diazabicyclo(5.4.0)undec-7-ene (382 mg, 2.5 mmol). The crude product is purified by flash chromatography (eluent: cyclohexane/ethyl acetate), and 422 mg (93% of theory) of the product are obtained after evaporation of the solvent.

Workup

  1. customThe crude product is purified by flash chromatography (eluent: cyclohexane/ethyl acetate), and 422 mg (93% of theory) of the product
  2. customare obtained
  3. customafter evaporation of the solvent

Sources & evidence

ORD record
ord-06d3f25f40d5413185c6bd6e4429eb50
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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