Ethyl Acetate → HCID 59380428, compound

HRID 2353846Notes

Reaction equation

HRID 2353846 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](/[CH:31]=[CH:32]/[C:33](OC)=[O:34])=[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.[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].CCOC(C)=O>C1COCC1>[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](/[CH:31]=[CH:32]/[CH2:33][OH:34])=[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 4

HCID 8857Ethyl AcetateHCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 59380391HCID 59380391, compound

Product 1

HCID 59380428HCID 59380428, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring and cold (0° C.) solution of methyl (2E)-3-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)[1]benzothieno[2,3-d]pyrimidin-7-yl]acrylate (400 mg, 0.77 mmol, 1 equiv) in THF (10 mL) was added diisobutylaluminum hydride in THF (1M, 3 mL, 3 mmol, 4 equiv). The resulting mixture was stirred at rt for 20 hn and it was then poured into the aq Rochelle's salt solution and EtOAc. This was filtered a pad of Celite®. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were concentrated and residue was triturated with hexane and ether to yield (250 mg, 67% yield). 1H-NMR (DMSO-d6) δ 8.93 (s, 1H), 8.43 (s, 1H), 8.41 (s, 1H), 8.1 (d, 1H), 7.67 (d, 1H), 7.60 (dd, 1H), 7.46 (dd, 1H), 7.39 (m, 1H), 7.24 (m, 2H), 7.17 (d, 1H), 7.10 (m, 1H), 6.49-6.65 (m, 2H), 5.20 (s, 2H), 4.90 (s, 1H), 4.11 (d, 2H); LCMS RT=3.71 min, [M+H]+=492.1.

Workup

  1. filtrationThis was filtered a pad of Celite®
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. concentrationThe combined organic layers were concentrated
  5. customresidue was triturated with hexane and ether
  6. customto yield (250 mg, 67% yield)

Sources & evidence

ORD record
ord-88ac821432ab4786b1a86f7f3c3e431b
Source dataset
uspto-grants-2010_07
Patent number
US07750017B2

Reaction notes

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