Diisobutylaluminumhydride → HCID 17989944, compound

HRID 1292967Notes

Reaction equation

HRID 1292967 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]1[CH2:35][CH2:34][C:9]2[C:10]3[C:15]([NH:16][C:17]4[CH:18]=[C:19]5[C:23](=[CH:24][CH:25]=4)[N:22]([CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:21]=[CH:20]5)=[N:14][CH:13]=[N:12][C:11]=3[S:33][C:8]=2[CH2:7]1)C.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[CH2:26]([N:22]1[C:23]2[C:19](=[CH:18][C:17]([NH:16][C:15]3[C:10]4[C:9]5[CH2:34][CH2:35][CH:6]([CH2:5][CH2:4][OH:3])[CH2:7][C:8]=5[S:33][C:11]=4[N:12]=[CH:13][N:14]=3)=[CH:25][CH:24]=2)[CH:20]=[N:21]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 58774537HCID 58774537, compound

Product 1

HCID 17989944HCID 17989944, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of THF (100 mL) was added 4.50 g (9.04 mmol, 1 equiv) of [4-(1-Benzyl-1H-indazol-5-ylamino)-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-7-yl]-acetic acid ethyl ester. A 1M solution of diisobutylaluminum hydride in THF (45.2 mL, 45.2 mmol, 5 equiv) was added to the solution at 0° C. and the reaction was stirred for 30 min before warming up to rt and stirring for 2 h. The reaction mixture was quenched with Rochelle's salt followed by EtOAc. The solution was separated and the aqueous layer discarded and the organic layer was washed with brine (200 mL) and water (100 mL). The resulting crude material was purified by flash chromatography eluting with 95/5 CH2Cl2/MeOH yielding 850 mg (21%) of Example 203 as a white solid. 1H-NMR (CD2Cl2) δ 8.36 (s, 1H), 8.08 (d, J=1.8 Hz, 1H), 8.01 (s, 1H), 7.46–7.19 (m, 8H), 5.60 (s, 2H), 3.77 (q, J=4.4 Hz, 2H), 3.21–2.96 (m, 3H), 2.56 (m, 1H), 2.11 (m, 2H), 1.67 (m, 3H), 1.45 (t, J=4.4 Hz, 1H). LCMS RT=2.68 min; [M+H]+=456.3.

Workup

  1. stirringstirring for 2 h
  2. customThe reaction mixture was quenched with Rochelle's salt
  3. customThe solution was separated
  4. washthe organic layer was washed with brine (200 mL) and water (100 mL)
  5. customThe resulting crude material was purified by flash chromatography
  6. washeluting with 95/5 CH2Cl2/MeOH yielding 850 mg (21%) of Example 203 as a white solid

Sources & evidence

ORD record
ord-f0549c75dece41c08f2c39731cef262a
Source dataset
uspto-grants-2007_07
Patent number
US07238701B2

Reaction notes

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