Hydrazine hydrate (1:1) → HCID 178425597, compound

HRID 1159462Notes

Reaction equation

HRID 1159462 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH:19][C:20]3[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)=[O:18])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1.O.[NH2:28][NH2:29]>C(O)CCC>[NH2:9][C:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][C:6]=2[C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=3)=[O:18])=[CH:12][CH:11]=2)[NH:29][N:28]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86242638HCID 86242638, compound

Product 1

HCID 178425597HCID 178425597, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of Example 35D (0.08 g, 0.22 mmol) and hydrazine hydrate (0.11 mL, 2.2 mmol) in n-butanol (5 mL) was heated at 110° C. for 2 h, then concentrated. The residue was purified via HPLC on an Agilent Zorbax Stablebond C-18 (7 micron particle size) preparative column using a solvent gradient of 20% to 100% acetonitrile in 0.1% aqueous TFA at a flow rate of 15 ml/min over 50 min, to give the title compound. 1H NMR (500 MHz, DMSO-D6) δ ppm 2.29 (s, 3H) 6.81 (d, J=7.32 Hz, 1H) 6.93 (d, J=4.58 Hz, 1H) 7.17 (t, J=7.63 Hz, 1H) 7.26 (d, J=7.63 Hz, 1H) 7.33 (s, 1H) 7.54 (d, J=8.24 Hz, 2H) 7.66 (d, J=7.93 Hz, 2H) 8.38 (d, J=4.27 Hz, 1H) 8.80 (s, 1H) 9.04 (s, 1H); MS (ESI(+)) m/e 359 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified via HPLC on an Agilent Zorbax Stablebond C-18 (7 micron particle size) preparative column
  3. customover 50 min

Sources & evidence

ORD record
ord-c75e71e6633c4bc98a6036877d21869b
Source dataset
uspto-grants-2010_10
Patent number
US07812166B2

Reaction notes

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