5-(6,7-Dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)pyridin-2-nitrile → 5-(6,7-Dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)pyridin-2-methylamine

HRID 84605Notes

Reaction equation

HRID 84605 reaction equation
[N:1]1[C:11]2[C:10]3[S:12][C:13]([C:15]4[CH:16]=[CH:17][C:18]([C:21]#[N:22])=[N:19][CH:20]=4)=[CH:14][C:9]=3[CH2:8][CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.O1CCCC1.[Pd]>[N:1]1[C:11]2[C:10]3[S:12][C:13]([C:15]4[CH:16]=[CH:17][C:18]([CH2:21][NH2:22])=[N:19][CH:20]=4)=[CH:14][C:9]=3[CH2:8][CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 1

HCID 668690225-(6,7-Dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)pyridin-2-nitrile

Product 1

HCID 579002045-(6,7-Dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)pyridin-2-methylamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 25 mg (0.082 mmol) of 5-(6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)pyridin-2-nitrile in 3 ml of acetic acid and 3 ml of tetrahydrofuran was subjected to hydrogenation over 40 mg of 5% palladium on charcoal for 4 hours. The catalyst was filtered off, the mother liquor was concentrated in vacuum. The residue was triturated with ethyl ether afforded a precipitate which was collected and dried in vacuum to give 319. Yield 24 mg (79%). MS: (ESI+) 310.0. 1H NMR (400 MHz, DMSO) δ 8.82 (s, 1H), 8.25 (dd, J=4.4, 1.1, 1H), 8.06 (dd, J=8.1, 1.9, 1H), 7.50 (d, J=9.9, 2H), 7.42 (dd, J=8.1, 1.1, 1H), 7.23 (dd, J=8.1, 4.5, 1H), 4.35 (t, J=4.6, 1H), 3.86 (s, 2H), 3.24 (t, J=4.6, 2H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe mother liquor was concentrated in vacuum
  3. customThe residue was triturated with ethyl ether
  4. customafforded a precipitate which
  5. customwas collected
  6. customdried in vacuum

Sources & evidence

ORD record
ord-c86fab0ba5a846728ec457609522ead3
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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