6-Methylpyridine-2-carboxylic acid → HCID 44539828, compound

HRID 1695793Notes

Reaction equation

HRID 1695793 reaction equation
ClC(N(C)C)=C(C)C.[CH3:9][C:10]1[N:15]=[C:14]([C:16]([OH:18])=O)[CH:13]=[CH:12][CH:11]=1.[NH2:19][C:20]1[CH:28]=[C:27]([C:29]2[CH:30]=[C:31]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[C:32]([Cl:35])=[N:33][CH:34]=2)[CH:26]=[C:25]2[C:21]=1[CH:22]=[N:23][N:24]2[CH3:41].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:35][C:32]1[N:33]=[CH:34][C:29]([C:27]2[CH:26]=[C:25]3[C:21]([CH:22]=[N:23][N:24]3[CH3:41])=[C:20]([NH:19][C:16]([C:14]3[CH:13]=[CH:12][CH:11]=[C:10]([CH3:9])[N:15]=3)=[O:18])[CH:28]=2)=[CH:30][C:31]=1[NH:36][S:37]([CH3:40])(=[O:39])=[O:38]

Participants

6

Reactant 4

HCID 702826-Methylpyridine-2-carboxylic acidHCID 516892Sodium BicarbonateHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 86653304HCID 86653304, compound

Product 1

HCID 44539828HCID 44539828, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

1-Chloro-N,N,2-trimethyl-1-propen-1-amine (0.042 ml) was added to 6-methyl-2-pyridinecarboxylic acid (44 mg) in DCM (1 ml). The reaction was stirred at RT for 20 mins. N-[5-(4-Amino-1-methyl-1H-indazol-6-yl)-2-chloro-3-pyridinyl]methanesulfonamide (75 mg) in DCM (2 ml) was added and the reaction stirred for 30 mins. Approximately 4 ml saturated sodium bicarbonate (aq) was added followed by DCM (3 ml). The reaction was stirred vigorously. The DCM was passed through a hydrophobic frit then evaporated to dryness. The residue was dissolved in DMSO:methanol (1 ml, 1:1, v/v) and purified by MDAP (method E). The pure fraction was evaporated to dryness to give title compound (6 mg)

Workup

  1. stirringthe reaction stirred for 30 mins
  2. stirringThe reaction was stirred vigorously
  3. customthen evaporated to dryness
  4. dissolutionThe residue was dissolved in DMSO
  5. custommethanol (1 ml, 1:1, v/v) and purified by MDAP (method E)
  6. customThe pure fraction was evaporated to dryness

Sources & evidence

ORD record
ord-89c4728f3106400da076ae4dcd23cb16
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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