Stannous chloride dihydrate → HCID 17985245, compound

HRID 1433040Notes

Reaction equation

HRID 1433040 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[S:22][C:21]4[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:20]=4[CH:19]=3)[CH2:13][C:12]2=[O:28])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[N:29]([O-])=O.[Na+].O.O.[Sn](Cl)Cl>Cl.O>[NH2:5][C:4]1[C:3]2[C:2](=[CH:9][C:8]([CH2:10][N:11]3[CH2:16][CH2:15][N:14]([CH2:17][C:18]4[S:22][C:21]5[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:20]=5[CH:19]=4)[CH2:13][C:12]3=[O:28])=[CH:7][CH:6]=2)[NH:1][N:29]=1

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 17985208HCID 17985208, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 17985245HCID 17985245, compoundYield 38.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Procedure

To a cooled solution (0° C.) of 2-Amino-4-[4-(6-chloro-benzo[b]thiophen-2-ylmethyl)-2-oxo-piperazin-1-ylmethyl]-benzonitrile (0.365 g, 0.89 mmol) in concentrated HCl (2.1 ml) is added dropwise a solution of sodium nitrite (0.068 g, 0.98 mmol) in H2O (0.2 ml). The reaction mixture is added to a cooled solution (0° C.) of tin (II) chloride dihydrate (1.61 g, 7.12 mmol) in concentrated HCl (0.62 ml) and H2O (3 ml). The precipitate is collected by vacuum filtration and dried under high vacuum. The crude solid is purified by column chromatography eluting with 10% 7M NH3 in CH3OH/CH2Cl2 to yield the title compound (0.144 g, 0.34 mmol) as a yellow solid. 1H NMR (DMSO, 300 MHz) δ11.35 (bs, 1H), 8.05 (d, 1H), 7.78 (d, 1H), 7.64 (d, 1H), 7.37 (m, 2H), 7.08 (s, 1H), 6.78 (d, 1H), 5.75 (s, 1H), 5.40 (bs, 1H), 4.58 (s, 2H), 3.88 (s, 2H), 3.20 (m, 4H), 2.70 (bt, 2H). MS (ion spray): m/z 426 (M+H)+. Anal. cald. for C21H20N5OSCl;(H2O)0.25: C, 58.6; H, 4.8; N, 16.3. Found C, 58.6; H, 4.7; N, 15.9. M.P.=246-248° C.

Workup

  1. filtrationThe precipitate is collected by vacuum filtration
  2. customdried under high vacuum
  3. customThe crude solid is purified by column chromatography
  4. washeluting with 10% 7M NH3 in CH3OH/CH2Cl2

Sources & evidence

ORD record
ord-54142bf58e0b47969bdcaaced79369e1
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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