Potassium Carbonate → HCID 66673215, compound

HRID 422213Notes

Reaction equation

HRID 422213 reaction equation
[C:1]([NH:8][CH2:9][CH:10]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl[C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[O:26])=[CH:23][N:22]=1.C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-]>CS(C)=O>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][CH:10]1[C:18]2[C:13](=[CH:14][C:15]([O:19][C:21]3[CH:29]=[CH:28][C:24]([C:25](=[O:26])[NH2:27])=[CH:23][N:22]=3)=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)([CH3:6])([CH3:7])[CH3:5]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 804566-ChloronicotinamideHCID 66673443HCID 66673443, compound

Product 1

HCID 66673215HCID 66673215, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Heat a mixture of N-Boc-1-aminomethyl-indan-5-ol (1.13 g, 4.29 mmol), 6-chloronicotinamide (671 mg, 4.29 mmol, K2CO3 (889 mg, 6.43 mmol), and DMSO (10 ml) at 100° C. for 19 hours. Pour the reaction mixture into saturated aqueous NH4Cl and extract with EtOAc. Wash extract with brine, dry (MgSO4) and concentrate to a brown foam. Purify on silica gel (30% EtOAc/DCM) to obtain [5-(5-carbamoyl-pyridin-2-yloxy)-indan-1-ylmethyl]-carbamic acid tert-butyl ester (847 mg) as a light yellow solid 1HNMR (CDCl3): 8.61 (s, 1H), 8.17 (d, 1H), 7.24 (d, 1H), 7.00 (s, 1H), 6.95 (m, 3H), 6.03 (br s, 2H), 4.65 (br s, 1H), 3.48 (m, 1H), 3.31 (m, 2H), 2.98-2.83 (m, 2H), 2.30 (m, 1H), 1.90 (m, 1H), 1.45 (s, 9H).

Workup

  1. temperatureHeat
  2. extractionextract with EtOAc
  3. washWash
  4. extractionextract with brine
  5. dry with materialdry (MgSO4)
  6. concentrationconcentrate to a brown foam
  7. customPurify on silica gel (30% EtOAc/DCM)

Sources & evidence

ORD record
ord-01be1df8cf2d4de8b22e851daf4cce9c
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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