Triethylamine → HCID 67278139, compound

HRID 1696245Notes

Reaction equation

HRID 1696245 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([N:9]2[C:13]3=[C:14]4[CH:20]=[CH:19][NH:18][C:15]4=[N:16][CH:17]=[C:12]3[NH:11][C:10]2=[O:21])[CH2:4]1.C(N(CC)CC)C.[N:29]([Si](C)(C)C)=[C:30]=[O:31]>CN1CCN(C)C1=O>[O:21]=[C:10]1[N:9]([C@@H:5]2[CH2:6][CH2:7][CH2:8][N:3]([C:30]([NH2:29])=[O:31])[CH2:4]2)[C:13]2=[C:14]3[CH:20]=[CH:19][NH:18][C:15]3=[N:16][CH:17]=[C:12]2[NH:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70696Trimethylsilyl isocyanateHCID 67277965HCID 67277965, compound

Product 1

HCID 67278139HCID 67278139, compound

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 1-[(3R)-3-piperidinyl]-3,6-dihydroimidazo-[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one dihydrochloride (20 mg) in 1,3-dimethyl-2-imidazolidinone (1 ml) was added triethylamine (51 μl) and isocyanato(trimethyl)silane (24 μl) which was stirred at 110° C. for 1 hour. The solvent was evaporated and purified by column chromatography on Hi-Flash™ (NH2)*(YAMAZEN CORPORATION) eluting with chloroform:methanol=100:0-85:15 to give (3R)-3-(2-oxo-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(2H)-yl)-1-piperidinecarboxamide (12 mg) as a white powder.

Workup

  1. customThe solvent was evaporated
  2. custompurified by column chromatography on Hi-Flash™ (NH2)*(YAMAZEN CORPORATION)
  3. washeluting with chloroform

Sources & evidence

ORD record
ord-d2f82a4fe6c843d3a76209e17eea6d62
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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