4-Aminobenzonitrile → HCID 86706289, compound

HRID 2205876Notes

Reaction equation

HRID 2205876 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.[NH2:30][C:31]1[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=1>>[C:26]([O:25][C:23]([N:21]1[CH:22]=[C:18]([C:9]2[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:4]3[CH:3]=[C:2]([NH:30][C:31]4[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=4)[N:7]=[CH:6][C:5]=3[CH:8]=2)[CH:19]=[N:20]1)=[O:24])([CH3:28])([CH3:27])[CH3:29]

Participants

3

Reactant 2

HCID 133964-AminobenzonitrileHCID 86706270HCID 86706270, compound

Product 1

HCID 86706289HCID 86706289, 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) (50 mg, 0.108 mmol) and 4-aminobenzonitrile (15.3 mg, 0.13 mmol, 1.2 eq) using the method described for Preparation 35 and using silica gel column chromatography eluting with EtOAc:hexane:triethylamine 10:10:1 (9 mg, 17%). 1H-NMR (500 MHz, CDCl3) 1.53 (s, 9H), 1.69 (s, 9H), 6.62 (s, 1H), 6.93 (s, 1H), 7.48 (d, J=8.8 Hz, 2H), 7.57 (d, J=8.8 Hz, 1H), 7.74 (s, 1H), 7.83 (s, 1H), 8.23 (s, 1H), 8.54 (s, 1H).

Workup

  1. customdescribed for Preparation 35
  2. washeluting with EtOAc:hexane:triethylamine 10:10:1 (9 mg, 17%)

Sources & evidence

ORD record
ord-cd12f460ff8b4039a0e84a6cc83b7e9c
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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