Hydrochloric Acid → HCID 10027941, compound

HRID 1293481Notes

Reaction equation

HRID 1293481 reaction equation
[N+](C1C=CC([C:10]2[CH:22]=[C:21]([C:23]([O-])=[O:24])[C:20]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]([CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:12]=3[C:11]=2[O:33][CH3:34])=CC=1)([O-])=O.[Cl:35][C:36]1[CH:37]=[N:38][CH:39]=[C:40]([Cl:43])[C:41]=1[NH2:42].[H-].[Na+].Cl>CN(C=O)C>[Cl:35][C:36]1[CH:37]=[N:38][CH:39]=[C:40]([Cl:43])[C:41]=1[NH:42][C:23]([C:21]1[C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:12]=2[C:11]([O:33][CH3:34])=[CH:10][CH:22]=1)=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 69282527HCID 69282527, compound

Product 1

HCID 10027941HCID 10027941, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-nitrophenyl-9-benzyl-1-methoxy-9H-4-carbazolecarboxylate (229 mg, 0.506 mmoles) and 3,5-dichloro-4-aminopyridine (82.53 mg, 0.506 mmoles) in dry DMF (10 ml), under N2 atmosphere, 60% sodium hydride (44.19 mg, 1.012 mmoles) was added at 25° C. and the reaction mixture was stirred overnight. The reaction mixture was poured into ice-cold water and neutralized with 1N HCl. The compound was extracted with chloroform (2×15ml), combined the organic layers and washed with water (3×15 ml) and with brine (15 ml). The organic layer was dried over anhydrous sodium sulphate and concentrated to give 200 mg of the crude compound which was purified by column chromatography to yield 139 mg of the title compound as light brown colored solid, m.p: 215-217° C.

Workup

  1. extractionThe compound was extracted with chloroform (2×15ml)
  2. washwashed with water (3×15 ml) and with brine (15 ml)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated
  5. customto give 200 mg of the crude compound which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-e160cd2480ed436dbb4f25b88803f5eb
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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