Hydrochloric Acid → HCID 58203820, compound

HRID 2385851Notes

Reaction equation

HRID 2385851 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-a609173ec01a4ed68016823b1902b539
Source dataset
uspto-grants-2012_09
Patent number
US08263633B2

Reaction notes

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