Ammonia → HCID 178462787, compound

HRID 1710370Notes

Reaction equation

HRID 1710370 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.[CH2:26]([N:28]1[CH2:33][CH2:32][N:31]([S:34](C2C=CC(C3C=C4N=C(CCC5NC(=S)CCCC5)NC4=NC=3)=CC=2)(=[O:36])=[O:35])[CH2:30][CH2:29]1)[CH3:27].N>CO>[CH2:26]([N:28]1[CH2:33][CH2:32][N:31]([S:34]([C:4]2[CH:3]=[CH:2][C:1]([C:7]3[CH:8]=[C:9]4[N:15]=[C:14]([CH2:16][CH2:17][CH:18]5[N:24]=[C:23]([NH2:25])[CH2:22][CH2:21][CH2:20][CH2:19]5)[NH:13][C:10]4=[N:11][CH:12]=3)=[CH:6][CH:5]=2)(=[O:35])=[O:36])[CH2:30][CH2:29]1)[CH3:27]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 178462789HCID 178462789, compound2×HCID 178508386HCID 178508386, compound2×

Product 1

HCID 178462787HCID 178462787, compound

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 157 mg of 7-(2-{6-[4-(4-ethyl-piperazine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}-ethyl)-azepane-2-thione (compound A7) and 6.90 ml of methanol containing ammonia (strength: 7.0 M) at 50° C. for 90 hours. Purification by flash chromatography on LiChroprep-NH2® (eluent gradient: ethyl acetate/0-100 vol. % 2-propanol) affords 28 mg of the title compound as an amorphous solid of m.p. 199° C. ESI-MS: 528.2 (MNH4+), 510.4 (MH+), TLC: Rf=0.30 (LiChroprep-NH2® HPTLC, neat methanol).

Workup

  1. customThe title compound is synthesized
  2. customPurification by flash chromatography on LiChroprep-NH2® (eluent gradient: ethyl acetate/0-100 vol. % 2-propanol)

Sources & evidence

ORD record
ord-bc66752fd7374c369e7886a7819b089f
Source dataset
uspto-grants-2010_09
Patent number
US07790710B2

Reaction notes

Loading…