2-chloro-N,N-dimethylacetamide → HCID 90413798, compound

HRID 1522019Notes

Reaction equation

HRID 1522019 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH2:18][C@@H:19]([CH2:23][OH:24])[NH:20][CH2:21][CH:22]=4)=[CH:16][C:9]=23)[CH:7]=1.C(N(C(C)C)C(C)C)C.Cl[CH2:37][C:38]([N:40]([CH3:42])[CH3:41])=[O:39]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH2:18][C@@H:19]([CH2:23][OH:24])[N:20]([CH2:37][C:38]([N:40]([CH3:42])[CH3:41])=[O:39])[CH2:21][CH:22]=4)=[CH:16][C:9]=23)[CH:7]=1

Participants

5

Reactant 3

HCID 758862-chloro-N,N-dimethylacetamideHCID 81531DiisopropylethylamineHCID 90412072HCID 90412072, compound

Product 1

HCID 90413798HCID 90413798, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of Example 260H (150 mg, 0.352 mmol) in N,N-dimethylformamide (1.8 mL) was added N-ethyl-N-isopropylpropan-2-amine (227 mg, 1.759 mmol) and 2-chloro-N,N-dimethylacetamide (39.9 μL, 0.387 mmol). The mixture was stirred for 3 days at room temperature and for 2 hours at 70° C., and partitioned between water and ethyl acetate (three times). The extracts were dried over sodium sulfate, filtered, and concentrated, and the residue was purified by flash chromatography on silica gel, eluting with a gradient of 0-8% methanol/dichloromethane to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.77 (s, 1H), 8.18 (d, J=5.0 Hz, 1H), 7.31-7.16 (m, 3H), 7.02 (d, J=5.0 Hz, 1H), 6.46 (s, 1H), 6.18 (d, J=1.8 Hz, 1H), 4.61 (t, J=5.3 Hz, 1H), 3.74 (s, 3H), 3.60-3.27 (m, 6H), 3.33 (s, 3H), 3.02 (s, 3H), 2.93 (dd, J=11.1, 5.7 Hz, 1H), 2.81 (s, 3H), 2.48-2.32 (m, 2H); MS (ESI+) m/z 439.0 (M+H)+.

Workup

  1. custompartitioned between water and ethyl acetate (three times)
  2. dry with materialThe extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by flash chromatography on silica gel
  6. washeluting with a gradient of 0-8% methanol/dichloromethane

Sources & evidence

ORD record
ord-d2bb6b97c87c4ac79e5406e1420a5abd
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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