Isopropylamine → HCID 68289239, compound

HRID 541241Notes

Reaction equation

HRID 541241 reaction equation
Cl[C:2]1[CH:33]=[CH:32][C:5]([C:6]([NH:8][C:9]2[CH:14]=[C:13]([C:15]([N:17]3[CH2:22][CH:21]4[CH:19]([CH:20]4[C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)[CH2:18]3)=[O:16])[CH:12]=[CH:11][C:10]=2[CH3:31])=[O:7])=[CH:4][N:3]=1.[CH:34]([NH2:37])([CH3:36])[CH3:35].C([O-])(O)=O.[Na+]>CS(C)=O>[CH:34]([NH:37][C:2]1[CH:33]=[CH:32][C:5]([C:6]([NH:8][C:9]2[CH:14]=[C:13]([C:15]([N:17]3[CH2:18][CH:19]4[CH:21]([CH:20]4[C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)[CH2:22]3)=[O:16])[CH:12]=[CH:11][C:10]=2[CH3:31])=[O:7])=[CH:4][N:3]=1)([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 516892Sodium BicarbonateHCID 86672527HCID 86672527, compound2×

Product 1

HCID 68289239HCID 68289239, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-chloro-N-(5-(6-(4-methoxyphenyl)-3-azabicyclo[3.1.0]hexane-3-carbonyl)-2-methylphenyl)nicotinamide (compound 118.11, 0.107 g, 0.23 mmol) and isopropylamine (1.5 mL) in DMSO (1.5 mL) was heated at 120° C. in a sealed pressure tube overnight. After cooling to room temperature, the reaction mixture was poured into saturated aqueous NaHCO3 and extracted with EtOAc (3×). The combined organic extract was dried over MgSO4, filtered and concentrated. The residue was triturated with hexane to give the title compound as a white powder (40 mg, 36% yield). MS [M+H]+: 485. 1H-NMR (DMSO-d6, 400 Hz) δ 9.63 (s, 1H), 8.69 (d, J=3 Hz, 1H), 7.95-7.90 (m, 1H), 7.55-7.51 (m, 1H), 7.39-7.30 (m, 2H), 7.10-7.03 (m, 3H), 6.84 (d, J=9.2 Hz, 2H), 6.52 (d, J=9.2 Hz, 1H), 4.17-4.07 (m, 2H), 3.85-3.77 (m, 1H), 3.74 (s, 3H), 3.65-3.51 (m, 2H), 2.30 (s, 3H), 1.87 (s, 2H), 1.69 (t, J=3.7 Hz, 1H), 1.20 (d, J=7.2 Hz, 6H).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc (3×)
  3. extractionThe combined organic extract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-f6353b39ccef46a2b95824113f69f67b
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

Loading…