Hydrochloric Acid → HCID 86679346, compound

HRID 1498923Notes

Reaction equation

HRID 1498923 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][NH:12][NH:13][C:14]([C:16]3[S:20][C:19]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=4[O:28][CH3:29])=[N:18][C:17]=3[CH3:30])=[O:15])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.C=O.B.N1C=CC=C[CH:35]=1.Cl.[OH-].[Na+]>CO.C(O)(=O)C>[CH3:35][N:12]([CH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[CH:3]=[CH:4]2)[NH:13][C:14]([C:16]1[S:20][C:19]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[O:28][CH3:29])=[N:18][C:17]=1[CH3:30])=[O:15]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 2723995Borane;pyridineHCID 86679347HCID 86679347, compound

Product 1

HCID 86679346HCID 86679346, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 2-(4-chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylic acid N′-(1-methyl-1H-indol-5-ylmethyl)hydrazide (100 mg) prepared in the Step 17-1, a 37% formaldehyde solution (23 mg), pyridine borane (0.07 ml), acetic acid (2 ml) and methanol (4 ml) was stirred at a room temperature for 41 hours. To the reaction solution, 10% hydrochloric acid (0.5 ml) was added, and the resulting mixture was stirred for 20 minutes. Thereafter, the resulting mixture was neutralized with a 1-N sodium hydroxide aqueous solution. The neutralized mixture was concentrated under a reduced pressure. Then, water was added thereto, and the mixture was subjected to extraction twice with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate solution and a saturated saline solution in order, dried over sodium sulfate, and concentrated under a reduced pressure. The concentrate was purified by a first thin-layer chromatography (chloroform:methanol=20:1) and then a second thin-layer chromatography (hexane:ethyl acetate=1:1) to give the title compound (22 mg, 21%).

Workup

  1. customprepared in the Step 17-1
  2. concentrationThe neutralized mixture was concentrated under a reduced pressure
  3. additionThen, water was added
  4. extractionthe mixture was subjected to extraction twice with ethyl acetate
  5. washThe organic layer was washed with a saturated sodium bicarbonate solution
  6. dry with materiala saturated saline solution in order, dried over sodium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customThe concentrate was purified by a first thin-layer chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-75496b75ef7b43ba95f436732f125b21
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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