Thionyl Chloride → HCID 66825776, compound

HRID 1468618Notes

Reaction equation

HRID 1468618 reaction equation
[NH2:1][N:2]1[C:10]2[C:6]([N:7]3[N:13]([CH2:14][CH:15]4[CH2:17][CH2:16]4)[C:12](=[O:18])[N:11]([CH2:19][CH2:20][N:21]4[CH:25]=[C:24]([C:26](O)=[O:27])[CH:23]=[N:22]4)[CH:8]3[N:9]=2)=[C:5]([C:29]2[O:30][CH:31]=[CH:32][CH:33]=2)[N:4]=[CH:3]1.S(Cl)(Cl)=O.[CH:38]1([NH2:41])[CH2:40][CH2:39]1>>[NH2:1][N:2]1[C:10]2[C:6]([N:7]3[N:13]([CH2:14][CH:15]4[CH2:17][CH2:16]4)[C:12](=[O:18])[N:11]([CH2:19][CH2:20][N:21]4[CH:25]=[C:24]([C:26]([NH:41][CH:38]5[CH2:40][CH2:39]5)=[O:27])[CH:23]=[N:22]4)[CH:8]3[N:9]=2)=[C:5]([C:29]2[O:30][CH:31]=[CH:32][CH:33]=2)[N:4]=[CH:3]1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 69828CyclopropylamineHCID 66824471HCID 66824471, compound

Product 1

HCID 66825776HCID 66825776, compoundYield 9.2%

Conditions

Temperature
75 °C

Procedure

A mixture of 1-[2-[5-amino-1-(cyclopropylmethyl)-8-(2-furyl)-2-oxo-[1,2,4]triazolo[5,1-f]purin-3-yl]ethyl]pyrazole-4-carboxylic acid (0.050 g, 0.111 mmol) was taken in thionyl chloride (0.04 ml, 0.557 mmol) and stirred at 75° C. for 2 hours. The reaction mixture was concentrated and residue was dissolved in DCM (2 ml). To the above solution cyclopropyl amine (0.015 ml, 0.222 mmol) was added at 0° C. and stirred at same temperature for 2 hours and filtered to obtain 1-[2-[5-amino-1-(cyclopropylmethyl)-8-(2-furyl)-2-oxo-[1,2,4]triazolo[5,1-f]purin-3-yl]ethyl]-N-cyclopropyl-pyrazole-4-carboxamide (5.0 mg, 9%) as an off white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionresidue was dissolved in DCM (2 ml)
  3. stirringstirred at same temperature for 2 hours
  4. filtrationfiltered

Sources & evidence

ORD record
ord-a19934e939f9458ca76ce6d627a260bf
Source dataset
uspto-grants-2015_04
Patent number
US09006177B2

Reaction notes

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