methyl 2-(1H-pyrazol-4-yl)acetate → (S)-1-(2-benzyl-4-(1-cyclobutyl-3-ethyl-1H-indazol-6-yl)piperazin-1-yl)-2-(1H-pyrazol-4-yl)ethanone

HRID 1423205Notes

Reaction equation

HRID 1423205 reaction equation
[CH2:1]([CH:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([CH2:27][CH3:28])=[N:19][N:20]3[CH:23]3[CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O:30][C:31](=O)[CH2:32][C:33]1[CH:34]=[N:35][NH:36][CH:37]=1>>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([CH2:27][CH3:28])=[N:19][N:20]3[CH:23]3[CH2:24][CH2:25][CH2:26]3)=[CH:16][CH:15]=2)[CH2:11][CH2:12][N:13]1[C:31](=[O:30])[CH2:32][C:33]1[CH:34]=[N:35][NH:36][CH:37]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 58189211methyl 2-(1H-pyrazol-4-yl)acetateHCID 668258696-(3-benzyl-piperazin-1-yl)-1-cyclobutyl-3-ethyl-1H-indazole

Product 1

HCID 58189071(S)-1-(2-benzyl-4-(1-cyclobutyl-3-ethyl-1H-indazol-6-yl)piperazin-1-yl)-2-(1H-pyrazol-4-yl)ethanoneYield 13%

Procedure

Prepared by the method outlined for Example 275 using 6-(3-benzyl-piperazin-1-yl)-1-cyclobutyl-3-ethyl-1H-indazole (185 mg, 0.494 mmol) and (1H-pyrazol-4-yl)-acetic acid methyl ester (148 mg, 1.06 mmol) with heating for 5 days to afford product as a colorless solid (31 mg, 13%). LC/MS (Method B) 3.70 min, [M+1]+ 483.

Workup

  1. customPrepared by the method
  2. temperaturewith heating for 5 days

Sources & evidence

ORD record
ord-a53f6e92674a48639811596c2c1ce531
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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