Dichloromethane methanol → HCID 137194527, compound

HRID 1350523Notes

Reaction equation

HRID 1350523 reaction equation
[CH:1]([N:4]1[N:13]=[C:12]2[C:6]([C:7]([NH2:18])=[N:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[NH:11]2)=[N:5]1)([CH3:3])[CH3:2].[CH2:19]([C@H:27]1[CH2:32][NH:31][CH2:30][CH2:29][NH:28]1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(Cl)[Cl:34].C[OH:37]>CN1C(=O)CCC1.O>[OH2:37].[ClH:34].[ClH:34].[CH:1]([N:4]1[N:13]=[C:12]2[C:6]([C:7]([N:18]3[CH2:30][CH2:29][NH:28][C@@H:27]([CH2:19][CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:32]3)=[N:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[NH:11]2)=[N:5]1)([CH3:3])[CH3:2].[CH:1]([N:4]1[N:13]=[C:12]2[C:6]([C:7]([N:31]3[CH2:30][CH2:29][NH:28][C@@H:27]([CH2:19][CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:32]3)=[N:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[NH:11]2)=[N:5]1)([CH3:3])[CH3:2].[ClH:34].[ClH:34]

Participants

6

Reactant 3

HCID 21226129Dichloromethane methanolHCID 44828673(S)-2-PhenethylpiperazineHCID 178456618HCID 178456618, compound

Product 1

HCID 137194527HCID 137194527, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Combine 2-isopropyl-2,4-dihydro-1,2,3,4,9-pentaaza-benzo[f]azulen-10-ylamine (0.863 g, 3.56 mmol), (S)-2-phenethyl-piperazine (0.678 g, 3.56 mmol) in NMP (6.0 mL) and heat at 200° C. for 3 hours. Cool to ambient temperature and dilute with water (75 mL). Extract with ethyl acetate to give 1.59 g of the crude product. Silica gel chromatography, eluding with methylene chloride:methanol (100:7.5), to give the title compound as the free base. The dihydrochloride salt precipitates in ethyl acetate as a yellow solid: mp 210° C.; mass spectrum (ion spray): m/z=416 (M+1); Analysis for C24H31Cl2N7(0.5 H2O): calcd: C, 57.95; H, 6.48; N, 19.71; found: C, 58.01; H, 6.22; N, 19.70.

Workup

  1. extractionExtract with ethyl acetate
  2. customto give 1.59 g of the crude product

Sources & evidence

ORD record
ord-c6e2224319024fddbb5d3657e3c46624
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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