HCID 178495628, compound → HCID 178495627, compound

HRID 1257698Notes

Reaction equation

HRID 1257698 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:29]([O-])=O)[C:18]([NH:19][C@H:20]4[CH2:25][CH2:24][C@H:23]([CH2:26][O:27][CH3:28])[CH2:22][CH2:21]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Fe].CO.O>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([NH2:29])[C:18]([NH:19][C@H:20]4[CH2:21][CH2:22][C@H:23]([CH2:26][O:27][CH3:28])[CH2:24][CH2:25]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 178495628HCID 178495628, compound

Product 1

HCID 178495627HCID 178495627, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of trans (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(4-methoxymethyl-cyclohexyl)-amine (1.92 g, 4.32 mmol), iron powder (0.96 g, 17.3 mmol) ammonium chloride (1.39 g, 26.0 mmol) and methanol/water (90 mL, 3:1) was stirred and heated at reflux for 1 hour. The cooled mixture was filtered through a pad of Celite® washing the filter cake with methanol. The combined filtrate was concentrated to dryness and the residue dissolved in DCM then purified by column chromatography on silica gel (eluting with 20%-50% ethyl acetate in DCM) affording 1.79 g (99%) of trans 1-benzenesulfonyl-N*4*-(4-methoxymethyl-cyclohexyl)-1H-pyrrolo[2,3-b]pyridine-4,5-diamine as a grey solid. LCMS (Method I, ESI): RT=2.49 min, m+H=415.2; 1H NMR (300 MHz, CDCl3): δ 8.14 (d, 2H), 7.81 (s, 1H), 7.57-7.39 (m, 4H), 6.55 (d, 1H), 4.70 (br s, 1H), 3.72-3.55 (m, 1H), 3.35 (s, 3H), 3.24 (d, 2H), 2.22-2.11 (m, 2H), 1.95-1.85 (m, 2H), 1.76-1.50 (m, 3H), 1.33-1.07 (m, 4H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. filtrationThe cooled mixture was filtered through a pad of Celite®
  4. washwashing the filter cake with methanol
  5. concentrationThe combined filtrate was concentrated to dryness
  6. dissolutionthe residue dissolved in DCM
  7. customthen purified by column chromatography on silica gel (eluting with 20%-50% ethyl acetate in DCM)

Sources & evidence

ORD record
ord-ae148b07e93745e0b9326dcdb60bb60d
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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