Hydrochloric Acid → HCID 44539934, compound

HRID 1695795Notes

Reaction equation

HRID 1695795 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([NH:24][C:25]([C:27]3[N:28]=[C:29]([CH3:32])[S:30][CH:31]=3)=[O:26])[C:12]3[C:16]([CH:17]=2)=[N:15][N:14](C2CCCCO2)[CH:13]=3)[CH:5]=[N:6][C:7]=1[Cl:8].[CH3:33][C:34]1[CH:35]=[CH:36][C:37]([O:44][CH3:45])=[C:38]([S:40](Cl)(=[O:42])=[O:41])[CH:39]=1.Cl>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[Cl:8][C:7]1[N:6]=[CH:5][C:4]([C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[N:14][NH:15]3)=[C:11]([NH:24][C:25]([C:27]3[N:28]=[C:29]([CH3:32])[S:30][CH:31]=3)=[O:26])[CH:10]=2)=[CH:3][C:2]=1[NH:1][S:40]([C:38]1[CH:39]=[C:34]([CH3:33])[CH:35]=[CH:36][C:37]=1[O:44][CH3:45])(=[O:42])=[O:41]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1451496-Methoxy-m-toluenesulfonyl chloride3×HCID 58255741N-[6-(5-Amino-6-chloro-3-pyridinyl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

Product 1

HCID 44539934HCID 44539934, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

N-[6-(5-Amino-6-chloro-3-pyridinyl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide (50 mg) was dissolved in pyridine (1 ml) and 5-methyl-2-(methyloxy)benzenesulfonyl chloride (35 mg) was added. The reaction was stirred at RT overnight. Further 5-methyl-2-(methyloxy)benzenesulfonyl chloride (35 mg) was added and the reaction was stirred at RT for 4 h. DMAP (3 mg) followed by 5-methyl-2-(methyloxy)benzenesulfonyl chloride (20 mg) was added and the reaction was stirred at RT overnight. The reaction was neutralised with 2M HCl (aq) and extracted into DCM. The DCM was evaporated and the residue was dissolved in DMSO:methanol (1 ml, 8:1, v/v) and purified by MDAP (method E). The desired fraction was evaporated to dryness and methanol (3 ml) and a few drops of 2M HCl (aq) were added and the reaction stirred for 2 h. The reaction was evaporated to dryness to give title compound (39 mg).

Workup

  1. stirringthe reaction was stirred at RT for 4 h
  2. additionwas added
  3. stirringthe reaction was stirred at RT overnight
  4. extractionextracted into DCM
  5. customThe DCM was evaporated
  6. dissolutionthe residue was dissolved in DMSO
  7. custommethanol (1 ml, 8:1, v/v) and purified by MDAP (method E)
  8. customThe desired fraction was evaporated to dryness and methanol (3 ml) and a few drops of 2M HCl (aq)
  9. additionwere added
  10. stirringthe reaction stirred for 2 h
  11. customThe reaction was evaporated to dryness

Sources & evidence

ORD record
ord-81b7af10fbd046d293c36bb2d61f6da6
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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