Aluminium lithium hydride → HCID 24803564, compound

HRID 1698072Notes

Reaction equation

HRID 1698072 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]3[S:15][C:16]4[CH:22]=[C:21]([NH:23][CH2:24]C(F)(F)F)[CH:20]=[CH:19][C:17]=4[N:18]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.CN1CCN(C2N=CC(C3SC4C=C(NC(=O)OCC)C=CC=4N=3)=CC=2)CC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH3:24][NH:23][C:21]1[CH:20]=[CH:19][C:17]2[N:18]=[C:14]([C:11]3[CH:12]=[N:13][C:8]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[CH:9][CH:10]=3)[S:15][C:16]=2[CH:22]=1

Participants

4

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 24803562HCID 24803562, compoundHCID 24803563HCID 24803563, compound

Product 1

HCID 24803564HCID 24803564, compound

Procedure

The title compound (11 mg, 38%) was prepared by reduction according to the method described for the preparation of 2-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-N-(2,2,2-trifluoroethyl)-1,3-benzothiazol-6-amine by the use of ethyl {2-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-1,3-benzothiazol-6-yl}carbamate (37 mg, 0.088 mmol) as starting material, and lithium aluminiumhydride (10 mg, 0.26 mmol) as reagent, with the following modification: The reaction mixture was stirred at reflux for 1 h then at r.t. o.n. The crude was purified by prep. HPLC, to give the title compound (11 mg) as a pale yellow solid. 1H NMR (MeOH-D4) δ 8.59 (d, 1H) 7.98 (dd, 1H) 7.56 (d, 1H) 6.93 (d, 1H) 6.82 (d, 1H) 6.73 (dd, 1H) 3.55-3.69 (m, 4H) 2.74 (s, 3H) 2.48-2.60 (m, 4H) 2.32 (s, 3H); MS m/z (M+H) 340.

Workup

  1. customThe title compound (11 mg, 38%) was prepared by reduction
  2. temperatureat reflux for 1 h
  3. customat r.t.
  4. customThe crude was purified by prep

Sources & evidence

ORD record
ord-60948edfaf0542248f82457c4ebea2ae
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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