Hydrochloric Acid → HCID 57916066, compound

HRID 1696249Notes

Reaction equation

HRID 1696249 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.ON1C2C=CC=CC=2N=N1.[S:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[C:37](O)=[O:38].Cl>CN(C)C=O.CCOC(C)=O.C(N(CC)CC)C>[S:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[C:37]([N: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)=[O:38]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 107002-Thiophenecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 67277965HCID 67277965, compound

Product 1

HCID 57916066HCID 57916066, compoundYield 71.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-[(3R)-3-piperidinyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one dihydrochloride (30 mg) and 1-hydroxybenzotriazole (18.4 mg) in N,N-dimethylformamide (0.72 mL) was added triethylamine (0.028 mL), 2-thiophenecarboxylic acid (15.1 mg), and WSCD.HCl (70 mg, 0.365 mmol). After stirring for 9 hours at ambient temperature, the reaction mixture was diluted with EtOAc, washed with saturated aqueous sodium hydrogencarbonate, water (×3), and brine, dried over MgSO4, evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to give 1-[(3R)-1-(2-thienylcarbonyl)-3-piperidinyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (24.0 mg) as a white crystals.

Workup

  1. washwashed with saturated aqueous sodium hydrogencarbonate, water (×3), and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-c63cb190d0054dec9f02f1b0a5eda716
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

Loading…