Hydrochloric Acid → HCID 67357867, compound

HRID 2353855Notes

Reaction equation

HRID 2353855 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[C:26]4[CH:27]=[CH:28][C:29]([O:31][CH2:32][CH:33]5[CH2:37][O:36]C(C)(C)[O:34]5)=[CH:30][C:25]=4[S:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.Cl.C(N(CC)CC)C>C(#N)C.CO.ClCCl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[C:26]4[CH:27]=[CH:28][C:29]([O:31][CH2:32][C@H:33]([OH:34])[CH2:37][OH:36])=[CH:30][C:25]=4[S:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 67359560HCID 67359560, compound

Product 1

HCID 67357867HCID 67357867, compoundYield 124.5%

Reagents, catalysts & solvents 2

HCID 21226129Dichloromethane methanolCatalystHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
45 °C

Procedure

[3-Chloro-4-(3-fluoro-benzyloxy)-phenyl]-[7-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)benzo[4,5]thieno[2,3-d]pyrimidin-4-yl]-amine (0.92 g, 2 mmol) was dissolved in acetonitrile (5 mL) and filtered through a filter paper and filter paper washed with acetonitrile (2 mL). To the clear brown solution at 45° C. was added concentrated hydrochloric acid (37%, 0.14 mL, 2 mmol). To the resultant solid was added acetonitrile (5.0 mL) and then another equivalent of concentrated hydrochloric acid (37%, 0.14 mL, 2 mmol). The mixture was stirred at 45° C. for 1.5 hours when the reaction was judged complete by TLC (3% MeOH/Dichloromethane+one drop of triethylamine). The mixture was cooled to room temperature, filtered, and the solid was washed with acetonitrile (15 mL) and dried under vacuum at 40° C. over P2O5 for 16-18 hours to give ((2R)-3-{[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino) [1]benzothieno[2,3-d]pyrimidin-7-yl]oxy}propane-1,2-diol hydrochloride (0.70 g, 77%).

Workup

  1. filtrationfiltered through a filter paper
  2. filtrationfilter paper
  3. washwashed with acetonitrile (2 mL)
  4. temperatureThe mixture was cooled to room temperature
  5. filtrationfiltered
  6. washthe solid was washed with acetonitrile (15 mL)
  7. dry with materialdried under vacuum at 40° C. over P2O5 for 16-18 hours

Sources & evidence

ORD record
ord-126ff539e4064943b911ae2907e0f290
Source dataset
uspto-grants-2010_07
Patent number
US07750017B2

Reaction notes

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