1,2-Dichloroethane → HCID 178518483, compound

HRID 624830Notes

Reaction equation

HRID 624830 reaction equation
[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13](/[CH:14]=[C:15]4/[C:16](=[O:21])[NH:17][C:18](=[O:20])[NH:19]/4)=[C:9]3[N:8]=[C:7]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH:6]=2)[CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.[CH:38]1([CH2:41][C:42](O)=[O:43])[CH2:40][CH2:39]1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN1C(=O)CCC1.CO>[CH:38]1([CH2:41][C:42]([N:25]2[CH2:26][CH2:27][N:22]([C:7]3[CH:6]=[C:5]([NH:4][CH:1]4[CH2:2][CH2:3]4)[N:10]4[N:11]=[CH:12][C:13](/[CH:14]=[C:15]5/[C:16](=[O:21])[NH:17][C:18](=[O:20])[NH:19]/5)=[C:9]4[N:8]=3)[CH2:23][CH2:24]2)=[O:43])[CH2:40][CH2:39]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 138440Cyclopropaneacetic acidHCID 178518481HCID 178518481, compound

Product 1

HCID 178518483HCID 178518483, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To (Z)-5-((7-(cyclopropylamino)-5-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (step b) (10 mg, 0.027 mmol) in 50.0 uL NMP, was added HOBT (4.4 mg, 0.032 mmol), cyclopropyl acetic acid (60 ul in 0.02M NMP solution), DIPEA (9.5 ul, 0.067 mmol) and EDC (7.8 mg, 0.040 mmol). The reaction mixture was stirred at room temperature for one hour. Diluted the reaction mixture with methanol and prepared by HPLC to yield (Z)-5-((5-(4-(2-cyclopropylacetyl)piperazin-1-yl)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione. LCMS (M+1=451)

Workup

  1. customprepared by HPLC

Sources & evidence

ORD record
ord-2e643c8de91748a397835ef02b982eee
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

Loading…