Benzenamine, 2-chloro-4-(methylsulfonyl)- → HCID 86706337, compound

HRID 2205955Notes

Reaction equation

HRID 2205955 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.[Cl:30][C:31]1[CH:37]=[C:36]([S:38]([CH3:41])(=[O:40])=[O:39])[CH:35]=[CH:34][C:32]=1[NH2:33]>>[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:33][C:32]4[CH:34]=[CH:35][C:36]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:37][C:31]=4[Cl:30])[N:7]=[CH:6][C:5]=3[CH:8]=2)[CH:19]=[N:20]1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 25801Benzenamine, 2-chloro-4-(methylsulfonyl)-HCID 86706270HCID 86706270, compound

Product 1

HCID 86706337HCID 86706337, 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 (Preparation 10) and 2-chloro-4-(methylsulfonyl)aniline using the method described for Example 35. Purified using preparative TLC eluting with 20% ethyl acetate in CH2Cl2. 1H-NMR (500 MHz, DMSO-d6) 1.46, 1.60 (2×s, 9H each), 3.21 (s, 3H), 6.90 (s, 1H), 7.74 (dd, J=2.2, 8.9 Hz, 1H), 7.91 (d, J=2.30 Hz, 1H), 7.93 (s, 1H), 8.07 (s, 1H), 8.30 (d, J=8.5 Hz, 1H), 8.52 (s, 1H), 8.57 (s, 1H), 8.98 (s, 1H).

Workup

  1. customPurified
  2. washeluting with 20% ethyl acetate in CH2Cl2

Sources & evidence

ORD record
ord-8af35fbcd86d408a956ebecd49852235
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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