Ammonia → HCID 178482878, compound

HRID 1710373Notes

Reaction equation

HRID 1710373 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][N:27]([CH2:56][CH:57]1[CH2:61][CH2:60][CH2:59][O:58]1)[S:28](C1C=CC(C2C=C3N=C(CCC4CCCCC(=S)N4)NC3=NC=2)=CC=1)(=[O:30])=[O:29].N>CO>[NH2:25][C:23]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]([CH2:17][CH2:16][C:14]2[NH:13][C:10]3=[N:11][CH:12]=[C:7]([C:1]4[CH:2]=[CH:3][C:4]([S:28]([N:27]([CH3:26])[CH2:56][CH:57]5[CH2:61][CH2:60][CH2:59][O:58]5)(=[O:29])=[O:30])=[CH:5][CH:6]=4)[CH:8]=[C:9]3[N:15]=2)[N:24]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 178482880HCID 178482880, compoundHCID 178508386HCID 178508386, compound2×

Product 1

HCID 178482878HCID 178482878, 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 114 mg of N-methyl-N-(tetrahydro-furan-2-ylmethyl)-4-{2-[2-(7-thioxo-azepan-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-benzenesulfonamide (compound A10) and 5.0 ml of methanol containing ammonia (strength: 7.0 M) at 50° C. for 64 hours. Purification by flash chromatography on RP-C8 resin (eluent: acetonitrile/water 2:1 parts by volume) and lyophilization from 1.0 ml of water and 3.0 ml of dioxane afford 14 mg of the title compound as an amorphous, colorless solid of m.p. 260° C. ESI-MS: 511.4 (MH+). TLC: Rf=0.17 (HPTLC RP-C18, acetonitrile/water 2:1 parts by volume).

Workup

  1. customThe title compound is synthesized
  2. customPurification by flash chromatography on RP-C8 resin (eluent: acetonitrile/water 2:1 parts by volume) and lyophilization from 1.0 ml of water and 3.0 ml of dioxane

Sources & evidence

ORD record
ord-b68e71524696419d893c15a8bcc95d53
Source dataset
uspto-grants-2010_09
Patent number
US07790710B2

Reaction notes

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