Hydrochloric Acid → HCID 66781552, compound

HRID 1095730Notes

Reaction equation

HRID 1095730 reaction equation
COCCOC1C=CN2C(C3C=CC4C(=C(N)C=CC=4)N=3)=CN=C2C=1.[F:26][C@H:27]1[C@@H:32]([NH:33][C:34]2[CH:35]=[CH:36][CH:37]=[C:38]3[C:43]=2[N:42]=[C:41]([C:44]2[N:48]4[CH:49]=[CH:50][C:51]([O:53][CH2:54][CH2:55][O:56][CH3:57])=[CH:52][C:47]4=[N:46][CH:45]=2)[CH:40]=[CH:39]3)[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28]1.Cl.O1CCOCC1>CO>[F:26][C@H:27]1[C@@H:32]([NH:33][C:34]2[CH:35]=[CH:36][CH:37]=[C:38]3[C:43]=2[N:42]=[C:41]([C:44]2[N:48]4[CH:49]=[CH:50][C:51]([O:53][CH2:54][CH2:55][O:56][CH3:57])=[CH:52][C:47]4=[N:46][CH:45]=2)[CH:40]=[CH:39]3)[CH2:31][CH2:30][NH:29][CH2:28]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131729516HCID 131729516, compoundHCID 131729517HCID 131729517, compound

Product 1

HCID 66781552HCID 66781552, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Preparation of N-(cis)-3-fluoropiperidin-4-yl)-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-amine: (cis)-tert-Butyl 3-fluoro-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ylamino)piperidine-1-carboxylate (0.050 g, 0.093 mmol) was dissolved in MeOH (1 mL) the solution was treated with 4 M hydrogen chloride in dioxane (0.583 ml, 2.33 mmol). The mixture was stirred at ambient temperature for 4 hours, then concentrated in vacuo. The residue was redissolved and re-concentrated from MeOH three times. This material was purified by silica gel chromatography, eluting with (6% NH4OH in MeOH)/ethyl acetate to provide the desired product (16 mg). 1H NMR (400 MHz, CDCl3) δ 9.89 (d, 1H), 8.14 (s, 1H), 8.05 (d, 1H), 7.77 (d, 1H), 7.38-7.29 (m, 1H), 7.08 (d, 1H), 7.02 (s, 1H), 6.85-6.74 (m, 2H), 6.30 (d, 1H), 4.89 (d, J=49 Hz, 1H), 4.26-4.19 (m, 2H), 3.87-3.78 (m, 2H), 3.79-3.69 (m, 1H), 3.54-3.42 (m, 1H), 3.48 (s, 3H), 3.27-3.18 (m, 1H), 3.04-2.87 (dd, 1H), 2.79 (t, 1H), 2.17-2.09 (m, 1H), 2.00-1.86 (brd, 1H), 1.81-1.67 (m, 1H), 1.30-1.22 (m, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was redissolved
  3. concentrationre-concentrated from MeOH three times
  4. customThis material was purified by silica gel chromatography
  5. washeluting with (6% NH4OH in MeOH)/ethyl acetate

Sources & evidence

ORD record
ord-3cbd03aa5fae4dbfa9fb23f6b7b6cbdb
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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