Water → HCID 68435226, compound

HRID 215994Notes

Reaction equation

HRID 215994 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 1M 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 OC and water (5 ml) was added carefully, followed by 1M 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. additionwas added carefully
  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-b7130b37064b41b9a42b8f1c9fea6b8a
Source dataset
uspto-grants-2012_06
Patent number
US08193215B2

Reaction notes

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