Aluminium lithium hydride → HCID 57463206, compound

HRID 1783843Notes

Reaction equation

HRID 1783843 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([NH:17][C:18]3[N:23]=[C:22]([C:24]4[N:31]5[C:27]([S:28][CH:29]=[CH:30]5)=[N:26][C:25]=4[C:32]4[CH:33]=[C:34]([CH:41]=[CH:42][CH:43]=4)[C:35](N(OC)C)=[O:36])[CH:21]=[CH:20][N:19]=3)[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([NH:17][C:18]3[N:23]=[C:22]([C:24]4[N:31]5[C:27]([S:28][CH:29]=[CH:30]5)=[N:26][C:25]=4[C:32]4[CH:33]=[C:34]([CH:41]=[CH:42][CH:43]=4)[CH:35]=[O:36])[CH:21]=[CH:20][N:19]=3)[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57590682HCID 57590682, compound

Product 1

HCID 57463206HCID 57463206, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(5-{2-[(R)-1-(4-chloro-benzenesulfonyl)-piperidin-3-ylamino]-pyrimidin-4-yl}-imidazo[2,1-b]thiazol-6-yl)-N-methoxy-N-methyl-benzamide (0.05 g, 0.078 mmol) in anhydrous tetrahydrofuran (THF) (3.0 mL) at 0° C. was added a solution of lithium aluminum hydride (LAH) (2.0 M in THF) (0.078 mL, 0.15 mmol). The mixture was stirred at 0° C. for 30 minutes, then quenched with methanol (0.5 mL), diluted with dichloromethane (5 mL), washed with a solution of 10% aqueous potassium sodium tartrate (5 mL), water (5 mL), dried over sodium sulfate and concentrated. Product was purified by flash chromatography on silica gel (methanol:dichloromethane:ethylacetate=0.5:7:2) to afford 0.033 g (73%) of the title compound as a pale yellow solid. M.p.=124-126° C.; 400 MHz 1H NMR (DMSO-d6 at 60° C.) δ: 10.06 (s, 1H), 8.70 (br. s, 1H), 8.14-8.12 (m, 2H), 7.96-7.91 (m, 2H), 7.77-7.74 (m, 2H), 7.70-7.64 (m, 3H), 7.43 (d, J=4.4 Hz, 1H), 7.15 (d, J=7.6 Hz, 1H), 6.39 (d, J=5.2 Hz, 1H), 3.93 (bs, 1H), 3.74-3.71 (m, 1H), 3.48-3.45 (m, 1H), 2.49-2.4 (m, 1H), 2.35 (t, J=10.8 Hz, 1H), 1.89-1.82 (m, 2H), 1.60-1.56 (m, 1H), 1.39-1.32 (m, 1H). LCMS: 580 [M+H].

Workup

  1. customquenched with methanol (0.5 mL)
  2. additiondiluted with dichloromethane (5 mL)
  3. washwashed with a solution of 10% aqueous potassium sodium tartrate (5 mL), water (5 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customProduct was purified by flash chromatography on silica gel (methanol:dichloromethane:ethylacetate=0.5:7:2)

Sources & evidence

ORD record
ord-4778e9adea704e30a5f454fbb8db3ba5
Source dataset
uspto-grants-2009_03
Patent number
US07501430B2

Reaction notes

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