Hydrochloric Acid → HCID 58203820, compound

HRID 1190529Notes

Reaction equation

HRID 1190529 reaction equation
F[C:2]1[C:7]([C:8]2[CH:9]=[CH:10][C:11]3[O:20][CH2:19][CH2:18][C:17]4[S:16][C:15]([C:21]5[N:22]([CH:26]([CH3:28])[CH3:27])[N:23]=[CH:24][N:25]=5)=[N:14][C:13]=4[C:12]=3[CH:29]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.C[O:32]CCOC>>[CH:26]([N:22]1[C:21]([C:15]2[S:16][C:17]3[CH2:18][CH2:19][O:20][C:11]4[CH:10]=[CH:9][C:8]([C:7]5[C:2](=[O:32])[NH:3][CH:4]=[CH:5][CH:6]=5)=[CH:29][C:12]=4[C:13]=3[N:14]=2)=[N:25][CH:24]=[N:23]1)([CH3:28])[CH3:27]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 80711,2-DimethoxyethaneHCID 58203865HCID 58203865, compound

Product 1

HCID 58203820HCID 58203820, compoundYield 89%

Conditions

Temperature
80 °C

Procedure

To a solution of 306 (0.275 g, 0.675 mmol) in DME (5 mL) was added 10% aq HCl (5 mL). The reaction mixture was allowed to stir and heat at 80° C. for 18 hours before cooling, concentrating under reduced pressure, and diluting with EtOAc. The solution was washed sequentially with water, and brine, before drying over MgSO4 and concentrating under reduced pressure to 50 mL of EtOAc and the solids were collected by filtration to give 330 (244 mg, 89%). 1H NMR (400 MHz, DMSO) δ 11.79 (s, 1H), 9.00 (t, J=15.9, 1H), 8.10 (s, 1H), 7.67 (ddd, J=16.8, 8.8, 5.2, 2H), 7.37 (d, J=5.1, 1H), 7.08 (d, J=8.4, 1H), 6.31 (t, J=6.7, 1H), 5.88 (dt, J=13.2, 6.6, 1H), 4.58-4.20 (m, 2H), 3.46 (t, J=5.0, 2H), 1.55 (d, J=6.6, 6H). MS (ESI(+)): m/z 406.1 (M+H)

Workup

  1. temperaturebefore cooling
  2. concentrationconcentrating under reduced pressure
  3. additiondiluting with EtOAc
  4. washThe solution was washed sequentially with water, and brine
  5. dry with materialbefore drying over MgSO4
  6. concentrationconcentrating under reduced pressure to 50 mL of EtOAc
  7. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-bfe333a205eb4146a1362b8d5f32b8d1
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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