Sodium hydride → HCID 21101714, compound

HRID 1353433Notes

Reaction equation

HRID 1353433 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+].Cl[C:32]1[N:37]=[CH:36][CH:35]=[CH:34][N:33]=1>C(Cl)Cl.CO>[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[N:37]=[CH:36][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

5

Reactant 3

HCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 21101724HCID 21101724, compound

Product 1

HCID 21101714HCID 21101714, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

As described for example 138, 4-(7-chloro-4-quinolinyl)-N-(3-hydroxycycloheptyl)-1-piperazinecarboxamide, NaH, and 2-chloropyrimidine are reacted to give the product after flash chromatography with CH2Cl2-MeOH. LC-MS: 481 (M++1). 1H NMR (CDCl3) δ 8.75 (d, 1H), 8.50 (d, 2H), 8.05 (s, 1H), 7.95 (d, 1H), 7.45 (d, 1H), 6.92 (t, 1H), 6.85 (d, 1H), 5.55 (m, 1H), 5.15 (m, 1H), 4.10 (m, 1H), 3.70 (m, 4H), 3.23 (m, 4H), 1.80–2.25 (m, 7H), 1.50–1.70 (m, 3H).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-fc2b585118484f499030c5cdee110dbd
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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