Dimethylformamide → 2-[4-(benzyloxy)phenyl]-N-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-4-yl]acetamide

HRID 1790087Notes

Reaction equation

HRID 1790087 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N=[C:23]=[N:24][C:25]([CH3:29])(C)[CH2:26][CH3:27])C.ON1C2C=CC=[CH:39][C:34]=2[N:33]=N1.[CH3:40][N:41]1[CH2:46][CH2:45]O[CH2:43][CH2:42]1.[CH3:47][N:48](C=O)C>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([NH:33][C:34]2[CH:39]=[CH:27][CH:26]=[C:25]3[C:29]=2[CH:47]=[N:48][N:24]3[CH2:23][CH2:40][N:41]2[CH2:46][CH2:45][CH2:43][CH2:42]2)=[O:18])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 810334-Benzyloxyphenylacetic acidHCID 22992078Ethyldimethylpropylcarbodiimide hydrochloride

Product 1

HCID 114196662-[4-(benzyloxy)phenyl]-N-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-4-yl]acetamide

Procedure

A mixture of Example 1C (42.0 mg, 0.183 mmol), (4-benzyloxy-phenyl)-acetic acid (47.0 mg, 0.194 mmol), ethyldimethylpropylcarbodiimide hydrochloride (43.0 mg, 0.225 mmol), N-hydroxybenzotriazole (30.0 mg, 0.222 mmol), N-methyl morpholine (46.0 mg, 0.455 mmol) in 2 mL of DMF was shaken for 6 hour. The mixture was concentrated under reduced pressure and the residue dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/MeOH and purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.66 (m, 4H), 2.49 (m, 4H), 2.91 (t, 2H, J=6.60), 3.76 (s, 2H), 4.42 (t, 2H, J=6.60), 5.14 (s, 2H), 7.03 (m, 2H), 7.31–7.50 (m, 9H), 7.68 (m, 1H), 8.30 (s, 1H), 10.16 (s, 1H); MS (DCI/NH3) m/z 455 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/MeOH
  3. custompurified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-7f56ba04eb234739b0d2989cc4666284
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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