Chloroform → HCID 67278485, compound

HRID 1696253Notes

Reaction equation

HRID 1696253 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][C@@H:17]([CH3:20])[C@@H:16]([N:21]3[C:25]4=[C:26]5[CH:32]=[CH:31][NH:30][C:27]5=[N:28][CH:29]=[C:24]4[NH:23][C:22]3=[O:33])[CH2:15]2)=[CH:12][CH:13]=1)=[O:6].O1CCCC1.CC([O-])(C)C.[K+].C(Cl)(Cl)Cl>O>[CH3:20][C@@H:17]1[CH2:18][CH2:19][N:14]([C:11]2[CH:12]=[CH:13][C:8]([N:7]3[CH2:2][CH2:3][CH2:4][C:5]3=[O:6])=[CH:9][N:10]=2)[CH2:15][C@@H:16]1[N:21]1[C:25]2=[C:26]3[CH:32]=[CH:31][NH:30][C:27]3=[N:28][CH:29]=[C:24]2[NH:23][C:22]1=[O:33]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 67278539HCID 67278539, compound

Product 1

HCID 67278485HCID 67278485, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of rel-4-chloro-N-{6-[(3R,4R)—4-methyl-3-(2-oxo-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(2H)-yl)piperidin-1-yl]pyridin-3-yl}butanamide (72 mg) and tetrahydrofuran (2.2 mL) was added potassium 2-methylpropan-2-olate (138 mg) at ambient temperature. The mixture was stirred for 0.5 hour then chloroform (10 mL) and H2O (4 mL) were added. The organic layer was separated and dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by column chromatography to give rel-1-{(3R,4R)-4-methyl-1-[5-(2-oxopyrrolidin-1-yl)pyridin-2-yl]piperidin-3-yl}-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (66 mg) as a colorless solid.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-539296d2e2c1406ea14376663867a330
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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