1,2-Dichloroethane → HCID 58208027, compound

HRID 2197558Notes

Reaction equation

HRID 2197558 reaction equation
[C:1]([O:5][C:6]([N:8]([CH:32]([CH3:34])[CH3:33])[C:9]1[S:10][C:11]([C:14]2[CH:15]=[C:16]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:17]3[N:18]([CH:20]=[C:21]([C:23](O)=[O:24])[N:22]=3)[CH:19]=2)=[CH:12][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=[N:45][C:43]=2C=1.CCN(CC)CC.CN>ClCCl>[CH:32]([N:8]([C:9]1[S:10][C:11]([C:14]2[CH:15]=[C:16]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:17]3[N:18]([CH:20]=[C:21]([C:23](=[O:24])[NH:45][CH3:43])[N:22]=3)[CH:19]=2)=[CH:12][N:13]=1)[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])([CH3:34])[CH3:33]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 582079096-(2-(Tert-butoxycarbonyl(isopropyl)-amino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylic acid

Product 1

HCID 58208027HCID 58208027, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(2-(tert-butoxycarbonyl(isopropyl)-amino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylic acid (100 mg, 0.21 mmol) in dichloromethane was treated with EDC (48 mg, 0.25 mmol), HOBT (34 mg, 0.25 mmol), Et3N (25 mg. 0.25 mmol), methylamine (2 M in THF: 3 ml, 6 mmol) and stirred at room temperature overnight. The reaction mixture was concentrated on a rotary evaporator and the residue purified by chromatography on silica gel using ethyl acetate/hexanes (50%) as eluent to give 30 mg (30% yield) of tert-butyl isopropyl(5-(2-(methylcarbamoyl)-8-phenylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl)carbamate as a white solid. LCMS (Conditions C): 4.26 min (RT); (M+H)+=492.43 (100%).

Workup

  1. concentrationThe reaction mixture was concentrated on a rotary evaporator
  2. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-46fe84d65e6a494e9738d6e6ea02e9ab
Source dataset
uspto-grants-2012_12
Patent number
US08338604B2

Reaction notes

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