Ammonia → 7-{2-[6-(4-Methoxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4,5,6,7-tetrahydro-3H-azepin-2-ylamine

HRID 1710367Notes

Reaction equation

HRID 1710367 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[N:15]=[C:14]([CH2:16][CH2:17][CH:18]4[N:24]=[C:23]([NH2:25])[CH2:22][CH2:21][CH2:20][CH2:19]4)[NH:13][C:10]3=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:26][O:27]C1C=CC(C2C=C3N=C(CCC4NC(=S)CCCC4)NC3=NC=2)=CC=1.N>CO>[CH3:26][O:27][C:4]1[CH:3]=[CH:2][C:1]([C:7]2[CH:8]=[C:9]3[N:15]=[C:14]([CH2:16][CH2:17][CH:18]4[N:24]=[C:23]([NH2:25])[CH2:22][CH2:21][CH2:20][CH2:19]4)[NH:13][C:10]3=[N:11][CH:12]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 178488745HCID 178488745, compound2×HCID 178508386HCID 178508386, compound2×

Product 1

HCID 1784887437-{2-[6-(4-Methoxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4,5,6,7-tetrahydro-3H-azepin-2-ylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound is synthesized as described for 7-[2-(6-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-4,5,6,7-tetrahydro-3H-azepin-2-ylamine (compound 1) from 98 mg of 7-{2-[6-(4-methoxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-azepane-2-thione (compound A3) and 6.0 ml of methanol containing ammonia (strength: 7.0 M) at 50° C. for 5 days. Purification by flash chromatography on LiChroprep-NH2® (eluent: ethanol) affords 23 mg of the title compound as an amorphous, colorless solid of m.p. 306° C. ESI-MS: 364.2 (MH+). TLC: Rf=0.50 (LiChroprep-NH2® HPTLC, methanol/water 10:1 parts by volume).

Workup

  1. customThe title compound is synthesized
  2. customPurification by flash chromatography on LiChroprep-NH2® (eluent: ethanol)

Sources & evidence

ORD record
ord-7c8f3373fa6646d3905f3a674d36b2ae
Source dataset
uspto-grants-2010_09
Patent number
US07790710B2

Reaction notes

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