Ammonium Chloride → HCID 178511272, compound

HRID 1257706Notes

Reaction equation

HRID 1257706 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:28]([O-])=O)[C:18]([NH:19][C@H:20]4[CH2:25][CH2:24][C@H:23]([C:26]#[N:27])[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.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:28][C:17]1[C:18]([NH:19][C@H:20]2[CH2:21][CH2:22][C@H:23]([C:26]#[N:27])[CH2:24][CH2:25]2)=[C:13]2[CH:12]=[CH:11][N:10]([S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[C:14]2=[N:15][CH:16]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 178511274HCID 178511274, compound

Product 1

HCID 178511272HCID 178511272, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of trans 4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexanecarbonitrile (5.00 g, 11.8 mmol), iron powder (−325 mesh, 2.59 g, 47.0 mmol) and ammonium chloride (3.74 g, 70.5 mmol) in a mixture of ethanol and water (3:1, 400 mL) was mechanically stirred at reflux for 4 hours. The cooled mixture was filtered through Celite®. The filtrate was concentrated under vacuum to low volume and the residue extracted into DCM (3×). The combined extracts were washed with water and brine, dried over sodium sulphate and concentrated under vacuum. Purification by diethyl ether trituration afforded 4.51 g (97%) of trans 4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexanecarbonitrile as a light grey solid. LCMS (Method Q, ESI): RT=2.69 min, m+H=396.1; 1H NMR (400 MHz, DMSO) δ: 8.02 (dd, 2H), 7.65 (m, 1H), 7.57 (m, 3H), 7.47 (d, 1H), 6.76 (d, 1H), 5.09 (d, 2H), 4.36 (s, 2H), 3.76 (m, 2H), 2.70 (m, 1H), 2.04 (dd, 2H), 1.94 (m, 2H), 1.72 (m, 2H), 1.29 (m, 2H).

Workup

  1. temperatureat reflux for 4 hours
  2. filtrationThe cooled mixture was filtered through Celite®
  3. concentrationThe filtrate was concentrated under vacuum to low volume
  4. extractionthe residue extracted into DCM (3×)
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under vacuum
  8. customPurification by diethyl ether trituration

Sources & evidence

ORD record
ord-7a3cc8e61c0c474c950ee9ba9f22b227
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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