4-(1H-pyrazol-1-ylmethyl)aniline → HCID 86706287, compound

HRID 2205874Notes

Reaction equation

HRID 2205874 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:18]3[CH:19]=[N:20][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:22]=3)[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:4]=2[CH:3]=1.[N:30]1([CH2:35][C:36]2[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=2)[CH:34]=[CH:33][CH:32]=[N:31]1>>[N:30]1([CH2:35][C:36]2[CH:42]=[CH:41][C:39]([NH:40][C:2]3[N:7]=[CH:6][C:5]4[CH:8]=[C:9]([C:18]5[CH:19]=[N:20][N:21]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH:22]=5)[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[C:4]=4[CH:3]=3)=[CH:38][CH:37]=2)[CH:34]=[CH:33][CH:32]=[N:31]1

Participants

3

Reactant 2

HCID 27644124-(1H-pyrazol-1-ylmethyl)anilineHCID 86706270HCID 86706270, compound

Product 1

HCID 86706287HCID 86706287, compound

Procedure

The title compound was prepared from tert-butyl 6-bromo-2-(1-(tert-butoxycarbonyl)-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (10) (70 mg, 0.15 mmol) and 4-((1H-pyrazol-1-yl)methyl)aniline (31.3 mg, 0.181 mmol, 1.2 eq), using the method described in Preparation 35 and using silica gel column chromatography eluting with EtOAc:hexane:triethylamine 10:10:1 (12 mg, 14.3%). 1H-NMR (500 MHz, CDCl3) 1.49 (s, 9H), 1.69 (s, 9H), 5.2 (s, 2H), 6.32 (s, 1H), 6.58 (s, 1H), 6.66 (d, J=8.3 Hz, 2H), 7 (d, J=8.5 Hz, 1H), 7.06 (d, J=8.3 Hz, 2H), 7.23 (d, J=8.5 Hz, 1H), 7.33 (m, 1H), 7.62 (s, 1H), 7.82 (s, 1H), 8.21 (s, 1H), 8.45 (s, 1H).

Workup

  1. customdescribed in Preparation 35
  2. washeluting with EtOAc:hexane:triethylamine 10:10:1 (12 mg, 14.3%)

Sources & evidence

ORD record
ord-d4130b9c6a09429d9d804cf6d12a80f7
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

Loading…