4-(2-Morpholinoethoxy)aniline → HCID 86706288, compound

HRID 2205875Notes

Reaction equation

HRID 2205875 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.[O:30]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][O:38][C:39]2[CH:45]=[CH:44][C:42]([NH2:43])=[CH:41][CH:40]=2)[CH2:32][CH2:31]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]([CH3:16])([CH3:15])[CH3:17])=[O:12])[C:4]3[CH:3]=[C:2]([NH:43][C:42]4[CH:44]=[CH:45][C:39]([O:38][CH2:37][CH2:36][N:33]5[CH2:32][CH2:31][O:30][CH2:35][CH2:34]5)=[CH:40][CH:41]=4)[N:7]=[CH:6][C:5]=3[CH:8]=2)[CH:19]=[N:20]1)=[O:24])([CH3:27])([CH3:28])[CH3:29]

Participants

3

Reactant 2

HCID 64847114-(2-Morpholinoethoxy)anilineHCID 86706270HCID 86706270, compound

Product 1

HCID 86706288HCID 86706288, 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) (100 mg, 0.216 mmol) and 4-(2-morpholinoethoxy)aniline (58 mg, 0.26 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 (20 mg, 15%). 1H-NMR (500 MHz, CDCl3) 1.45 (s, 9H), 1.67 (s, 9H), 2.58 (m, 4H), 2.8 (t, J=5.8 Hz, 2H), 3.73 (m, 4H), 4.11 (t, J=5.8 Hz, 2H), 6.54 (s, 1H), 6.6 (s, 1H), 6.91 (d, J=8.9 Hz, 2H), 7.27 (d, J=8.9 Hz, 2H), 7.37 (s, 1H), 7.8 (s, 1H), 8.19 (s, 1H), 8.39 (s, 1H).

Workup

  1. customdescribed in Preparation 35
  2. washeluting with EtOAc:hexane:triethylamine 10:10:1 (20 mg, 15%)

Sources & evidence

ORD record
ord-1127c26dd9014607bb1ce906f4ac65fa
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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