Sodium hydride → HCID 21101718, compound

HRID 1353435Notes

Reaction equation

HRID 1353435 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH:21]4[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]([OH:28])[CH2:22]4)=[O:19])[CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[H-].[Na+].Br[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[CH:34][N:33]=1>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH:21]4[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]([O:28][C:32]5[CH:37]=[C:36]([CH3:38])[CH:35]=[CH:34][N:33]=5)[CH2:22]4)=[O:19])[CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 27340872-Bromo-4-methylpyridineHCID 21101724HCID 21101724, compound

Product 1

HCID 21101718HCID 21101718, compound

Procedure

As described for example 138, 4-(7-chloro-4-quinolinyl)-N-(3-hydroxycycloheptyl)-1-piperazinecarboxamide, NaH, and 2-bromo-4-picoline are reacted to give the product. LC-MS 494 (M++1). 1H NMR (CDCl3) δ 8.75 (d, 1H), 8.05 (s, 1H), 7.98 (d, 1H), 7.85 (d, 1H), 7.45 (d, 1H), 6.85 (d, 1H), 6.68 (d, 1H), 6.56 (s, 1H), 6.20 (d, 1H), 5.16 (m, 1H), 4.10 (m, 1H), 3.78 (m, 4H), 3.25 (m, 4H), 2.25 (s, 3H), 2.10 (m, 3H), 1.85 (m, 2H), 1.30–1.73 (m, 5H).

Workup

  1. customare reacted
  2. customto give the product

Sources & evidence

ORD record
ord-5ea67298a8924bafb91743e2b2c6353b
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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