Water → HCID 67352516, compound

HRID 1257668Notes

Reaction equation

HRID 1257668 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:30]([O-])=O)[C:18]([NH:19][CH:20]4[CH2:25][CH2:24][CH2:23][CH:22]([O:26][C:27](=[O:29])[CH3:28])[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+].O>C(O)C.[Fe]>[NH2:30][C:17]1[C:18]([NH:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH:22]([O:26][C:27](=[O:29])[CH3:28])[CH2:21]2)=[C:13]2[CH:12]=[CH:11][N:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:9])=[O:8])[C:14]2=[N:15][CH:16]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 67343594HCID 67343594, compound

Product 1

HCID 67352516HCID 67352516, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Acetic acid 3-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexyl ester (trans racemic) (9.72 g, 21.2 mmol), ammonium chloride (2.26 g, 42.40 mmol), iron powder (5.92 g, 106 mmol), and water (15.0 mL) in ethanol (150 ml) was heated at 80° C. overnight. The reaction was followed by LC/MS to completion. On completion, the reaction mixture was used as is for the next step without any workup. LCMS (Method M, ESI): RT=1.90 min, m+H=428.9.

Sources & evidence

ORD record
ord-84fec5e5b421479895ca2a9b33b1a304
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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