Water → HCID 58712681, compound

HRID 2376709Notes

Reaction equation

HRID 2376709 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][C:17]2[C:22]([C:23](=O)[NH2:24])=[CH:21][N:20]=[C:19]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:34])[CH:18]=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:35])[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][CH:12]([CH2:15][NH:16][C:17]2[C:22]([C:23]#[N:24])=[CH:21][N:20]=[C:19]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:34])[CH:18]=2)[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 58712685HCID 58712685, compound

Product 1

HCID 58712681HCID 58712681, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (4-{[5-carbamoyl-2-(2-chloro-benzylamino)-pyridin-4-ylamino]-methyl}-cyclohexylmethyl)-carbamic acid tert-butyl ester (31 mg, 0.062 mmol) in CH2Cl2 at ambient temperature was added Burgess reagent (40 mg, 0. 168 mmol) in portions over 3 h. The resultant mixture was stirred at 25° C. for another 1 h and then water was added. The mixture was stirred for 20 min and extracted with CH2Cl2 (2×15 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica-gel column chromatography (hexanes/EtOAc, 2:1 v/v then EtOAc) to afford (4-{[2-(2-chloro-benzylamino)-5-cyano-pyridin-4-ylamino]-methyl}-cyclohexylmethyl)-carbamic acid tert-butyl ester as a white solid (12 mg, 40%).

Workup

  1. extractionextracted with CH2Cl2 (2×15 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica-gel column chromatography (hexanes/EtOAc, 2:1 v/v

Sources & evidence

ORD record
ord-477e428963cb4b2585a29bddfa8d4139
Source dataset
uspto-grants-2008_12
Patent number
US07468382B2

Reaction notes

Loading…