Diisopropylethylamine → HCID 67479945, compound

HRID 1752284Notes

Reaction equation

HRID 1752284 reaction equation
[NH2:1][C:2]1[C:3]([NH:9][C@@H:10]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.CCN(C(C)C)C(C)C.Cl[C:32](Cl)([O:34]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Cl:8][C:6]1[CH:7]=[C:2]2[NH:1][C:32](=[O:34])[N:9]([C@@H:10]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]3)[C:3]2=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 67479833HCID 67479833, compound

Product 1

HCID 67479945HCID 67479945, compoundYield 189%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of (R)-tert-butyl 3-(3-amino-5-chloropyridin-2-ylamino)pyrrolidine-1-carboxylate (680 mg, 2.2 mmol) and i-Pr2NEt (1.2 mL, 6.6 mmol0 in CH2Cl2 (50 mL) was cooled in an ice bath and solid triphosgene (213 mg, 0.72 mmol) was added. The ice bath was allowed to melt and the mixture was stirred overnight at rt. The mixture was concentrated to leave a black solid which was purified by chromatography on a 12-g silica cartridge eluted with a 0-100% EtOAc in hexanes gradient to afford (R)-tert-butyl 3-(6-chloro-2-oxo-1H-imidazo[4,5-b]pyridin-3(2H)-yl)pyrrolidine-1-carboxylate (461 mg, 62%) as a black solid. LC-MS Method 1 tR=1.65 min, m/z=339, 283.

Workup

  1. concentrationThe mixture was concentrated
  2. customto leave a black solid which
  3. customwas purified by chromatography on a 12-g silica cartridge
  4. washeluted with a 0-100% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-afa9ec8acca545c7a54173ea8d01ec58
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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