Water → HCID 68435226, compound

HRID 2104107Notes

Reaction equation

HRID 2104107 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[N:11]=[C:10]2[S:12][CH:13]=[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]2=[C:8]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[CH:7]=1)C.[H-].C([Al+]CC(C)C)C(C)C.O.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[C:15]1([C:14]2[C:9]3[C:10](=[N:11][C:6]([CH2:5][CH2:4][OH:3])=[CH:7][C:8]=3[NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[S:12][CH:13]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 68435332{3-Phenyl-4-[(pyridin-2-ylmethyl)-amino]-thieno[2,3-b]pyridin-6-yl}-acetic acid ethyl ester

Product 1

HCID 68435226HCID 68435226, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

{3-Phenyl-4-[(pyridin-2-ylmethyl)-amino]-thieno[2,3-b]pyridin-6-yl}-acetic acid ethyl ester (47 mg, 0.12 mmol) was dissolved in dry THF (10 ml) under nitrogen and cooled to 0° C. Diisobutyl Aluminium Hydride (0.466 ml of a 1 M solution in hexanes, 0.466 mmol) was added dropwise over 2 min and the mixture stirred at 0° C. for 1 h, then stirred at room temperature overnight. The reaction was cooled to 0° C. and water (5 ml) was added carefully, followed by 1 M Rochelle's salt (5 ml). The reaction was stirred at room temperature for 15 min, and then extracted with DCM (2×25 ml), the extracts combined, dried over magnesium sulphate, and concentrated. The residue was purified on silica, eluting (Ethyl Acetate/Petroleum ether), 50-100%) to give 2-{3-Phenyl-4-[(pyridin-2-ylmethyl)-amino]-thieno[2,3-b]pyridin-6-yl}-ethanol as a brown solid. Yield=25.3 mg (60.4%).

Workup

  1. stirringstirred at room temperature overnight
  2. temperatureThe reaction was cooled to 0° C.
  3. stirringThe reaction was stirred at room temperature for 15 min
  4. extractionextracted with DCM (2×25 ml)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified on silica
  8. washeluting (Ethyl Acetate/Petroleum ether), 50-100%)

Sources & evidence

ORD record
ord-1357afc103b048d99d6beb46b6bf3073
Source dataset
uspto-grants-2009_08
Patent number
US07576212B2

Reaction notes

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