1,2-Dichloroethane → HCID 178473882, compound

HRID 2281524Notes

Reaction equation

HRID 2281524 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:25]=[C:24]4[C:20]([N:21]=[CH:22][NH:23]4)=[C:19]([N:26]4[CH2:31][CH2:30][CH2:29][CH:28]([C:32](O)=[O:33])[CH2:27]4)[N:18]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C1C=CC2N(O)N=[N:41]C=2C=1.C(Cl)CCl.N>CN(C=O)C>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:25]=[C:24]4[C:20]([N:21]=[CH:22][NH:23]4)=[C:19]([N:26]4[CH2:31][CH2:30][CH2:29][CH:28]([C:32]([NH2:41])=[O:33])[CH2:27]4)[N:18]=3)=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 111,2-Dichloroethane2×HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 178473883HCID 178473883, compound

Product 1

HCID 178473882HCID 178473882, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-(4-(4-acetylpiperazin-1-yl)phenylamino)-9H-purin-6-yl)piperidine-3-carboxylic acid (40 mg, 0.086 mmol) and HOBt (30 mg, 0.196 mmol) in DMF (2 mL), EDC (35 mg, 0.183 mmol) was added. After being stirred for 90 min, NH3 (0.5 M in dioxane, 1.00 mL, 0.500 mmol) was added. The mixture was stirred for 2 h. More EDC (52 mg, 0.271 mmol) was added. It was stirred for another 20 h. The mixture was then purified by HPLC to give the titled compound (30 mg). MS 464.3 (M+H); UV 204.8, 273.8 nm.

Workup

  1. stirringThe mixture was stirred for 2 h
  2. stirringIt was stirred for another 20 h
  3. customThe mixture was then purified by HPLC

Sources & evidence

ORD record
ord-8e14a2403f67417a90c23824f49a55fd
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

Loading…