Hydrochloric Acid → HCID 44539935, compound

HRID 1695796Notes

Reaction equation

HRID 1695796 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].[CH:33]1([S:36](Cl)(=[O:38])=[O:37])[CH2:35][CH2:34]1.Cl.C(Cl)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:36]([CH:33]1[CH2:35][CH2:34]1)(=[O:38])=[O:37]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 2760919Cyclopropanesulfonyl chloride4×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 44539935HCID 44539935, compoundYield 28.8%

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 (40 mg) was dissolved in pyridine (1 ml) and cyclopropanesulfonyl chloride (24 mg) was added. The reaction was stirred at RT for 1 h. DMAP (3 mg) and cyclopropanesulfonyl chloride (24 mg) were added and the reaction was stirred for 1 h. Further cyclopropanesulfonyl chloride (48 mg) was added and the reaction stirred overnight. Further cyclopropanesulfonyl chloride (48 mg) was added and the reaction was stirred for 2 h. 2M HCl (aq) and DCM were added and the DCM was separated, passed through a hydrophobic frit and evaporated to dryness. The residue was dissolved in DMSO:methanol (1 ml, 7:3, v/v) and purified by MDAP (method E). The product 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 (12 mg).

Workup

  1. stirringthe reaction was stirred for 1 h
  2. stirringthe reaction stirred overnight
  3. stirringthe reaction was stirred for 2 h
  4. customthe DCM was separated
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in DMSO
  7. custommethanol (1 ml, 7:3, v/v) and purified by MDAP (method E)
  8. customThe product 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-e9ad14a7f55548fcaefe2fb07f4fcdc8
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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