Ammonia → HCID 178508387, compound

HRID 1710369Notes

Reaction equation

HRID 1710369 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.[N:26]1([S:30](C2C=CC(C3C=C4N=C(CCC5NC(=S)CCCC5)NC4=NC=3)=CC=2)(=[O:32])=[O:31])[CH2:29][CH2:28][CH2:27]1.N>CO>[N:26]1([S:30]([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:32])=[O:31])[CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 178508386HCID 178508386, compound2×HCID 178527293HCID 178527293, compound2×

Product 1

HCID 178508387HCID 178508387, 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 92 mg of 7-(2-{6-[4-(azetidine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}-ethyl)-azepane-2-thione (compound A6) and 4.50 ml of methanol containing ammonia (strength: 7.0 M) at 50° C. for 70 hours. Purification by flash chromatography on LiChroprep-NH2® (eluent gradient: dichloromethane/0-100 vol. % methanol) affords 56 mg of the title compound as an amorphous solid of m.p. 154° C. (decomp.). ESI-MS: 453.2 (MH+). TLC: Rf=0.23 (LiChroprep-NH2® HPTLC, neat methanol).

Workup

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

Sources & evidence

ORD record
ord-6a54087305ca4b91a12562cd65976e0a
Source dataset
uspto-grants-2010_09
Patent number
US07790710B2

Reaction notes

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