Diisobutylaluminum hydride → HCID 11948420, compound

HRID 1518033Notes

Reaction equation

HRID 1518033 reaction equation
COC1N=C2C(=CC=1)N=CC=C2N1C=C2C(CCC(NCCCC3C=CC=CC=3C)C2)=N1.[CH3:33][O:34][C:35]1[N:36]=[C:37]2[C:42](=[CH:43][CH:44]=1)[N:41]=[CH:40][CH:39]=[C:38]2[N:45]1[CH:53]=[C:52]2[C:47]([CH2:48][CH2:49][CH:50]([NH:54][C:55](=O)[CH2:56][CH2:57][C:58]3[CH:63]=[CH:62][C:61]([CH3:64])=[CH:60][CH:59]=3)[CH2:51]2)=[N:46]1.CC(C[AlH]CC(C)C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C(Cl)Cl.O>[CH3:33][O:34][C:35]1[N:36]=[C:37]2[C:42](=[CH:43][CH:44]=1)[N:41]=[CH:40][CH:39]=[C:38]2[N:45]1[CH:53]=[C:52]2[C:47]([CH2:48][CH2:49][CH:50]([NH:54][CH2:55][CH2:56][CH2:57][C:58]3[CH:63]=[CH:62][C:61]([CH3:64])=[CH:60][CH:59]=3)[CH2:51]2)=[N:46]1

Participants

7

Reactant 4

HCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 68495160HCID 68495160, compoundHCID 68499954HCID 68499954, compound

Product 1

HCID 11948420HCID 11948420, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

[2-(6-Methoxy-[1,5]naphthyridin-4-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl]-(3-o-tolyl-propyl)-amine. A solution of N-[2-(6-methoxy-[1,5]naphthyridin-4-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl]-3-p-tolyl-propionamide (0.020 g, 0.045 mmol) in CH2Cl2 (2 mL) was treated with DIBAL-H (1 M solution in THF, 0.45 mL, 0.45 mmol) at −78° C. for 30 min. The reaction mixture was warmed to 0° C. and stirred for 20 min, then at RT for 1 h. Satd. potassium sodium tartrate solution (5 mL) was added at −30° C. The solution was warmed to RT and stirred for 1 h. Water (10 mL) was added, and the aqueous layer was extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine (15 mL), dried (MgSO4), filtered, and concentrated. The crude was purified on SiO2 (0-5% CH3OH/CH2Cl2) to give 10 mg (53%) of the title compound as a clear oil. MS (ESI): exact mass calculated for C26H29N5O, 427.24; m/z found, 428.5 [M+H]+. 1H NMR (400 MHz, CDCl3): 9.10 (s, 1H), 8.77 (d, J=5.1, 1H), 8.26 (d, J=9.1, 1H), 8.15 (d, J=5.1, 1H), 7.19 (d, J=9.1, 1H), 7.09 (s, 4H), 4.10 (s, 3H), 3.03-2.95 (m, 3H), 2.84-2.76 (m, 3H), 2.68-2.64 (m, 2H), 2.54-2.50 (m, 1H), 2.31 (s, 3H), 2.15-2.13 (m, 1H), 1.91-1.80 (m, 4H).

Workup

  1. waitat RT for 1 h
  2. temperatureThe solution was warmed to RT
  3. stirringstirred for 1 h
  4. extractionthe aqueous layer was extracted with EtOAc (3×30 mL)
  5. washThe combined organic layers were washed with brine (15 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude was purified on SiO2 (0-5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-ae5afcdc5c1b4c30b9ed95f9fb70915c
Source dataset
uspto-grants-2012_07
Patent number
US08232391B2

Reaction notes

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