5-Phenyl-6-[4-({[4-(1,2,3-thiadiazol-4-yl)benzyl]amino}methyl)phenyl]nicotinonitrile → HCID 178420071, compound

HRID 2219071Notes

Reaction equation

HRID 2219071 reaction equation
[C:1]1([C:7]2[C:8]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][NH:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([C:30]5[N:31]=[N:32][S:33][CH:34]=5)=[CH:26][CH:25]=4)=[CH:17][CH:16]=3)=[N:9][CH:10]=[C:11]([CH:14]=2)[C:12]#[N:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:35]=[N+:36]=[N-:37].[Na+].O>[Zn+2].[Br-].[Br-].O>[C:1]1([C:7]2[C:8]([C:15]3[CH:16]=[CH:17][C:18]([CH2:21][NH:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([C:30]5[N:31]=[N:32][S:33][CH:34]=5)=[CH:26][CH:25]=4)=[CH:19][CH:20]=3)=[N:9][CH:10]=[C:11]([C:12]3[NH:37][N:36]=[N:35][N:13]=3)[CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 99120615-Phenyl-6-[4-({[4-(1,2,3-thiadiazol-4-yl)benzyl]amino}methyl)phenyl]nicotinonitrileHCID 86609354Water sodium azide

Product 1

HCID 178420071HCID 178420071, compound

Reagents, catalysts & solvents 1

HCID 86609355ZnBr2 waterCatalyst

Procedure

A mixture of 5-phenyl-6-[4({[4-(1,2,3-thiadiazol-4-yl)benzyl]amino}methyl)phenyl]nicotinonitrile (1-5; TFA salt) (69 mg, 0.1 mmol), 2M of NaN3 water solution (0.75 mL, 1.5 mmol), 2M of ZnBr2 water solution (0.5 mL, 1.0 mmol) was microwaved (Smith-Synthesizer) at 165° C. for 15 min. After this time, the solution was concentrated. The residue was re-dissolved in DMSO (1 mL) and purified by LCMS to afford the pure desired product (TFA salt) as a slightly yellow solid (1-6). Analytical LCMS: single peak (214 nm), 2.339 min. 1H NMR (500 MHz, DMSO-d6): δ 9.70 (s, 1H), 9.32 (d, J=2.1 Hz, 1H), 8.42 (d, J=2.1 Hz, 1H), 8.22 (d, J=8.2 Hz, 2H), 7.68 (d, J=8.3 Hz, 2H), 7.42-7.48 (M, 4H), 7.35-7.40 (m,3H), 7.28-7.32 (m, 2H), 4.26 (s, 2H), 4.23 (s, 2H); HRMS, calc'd for C28H22N8S (M+1), 503.1761; found 503.1769.

Workup

  1. customwas microwaved (Smith-Synthesizer) at 165° C. for 15 min
  2. concentrationAfter this time, the solution was concentrated
  3. dissolutionThe residue was re-dissolved in DMSO (1 mL)
  4. custompurified by LCMS

Sources & evidence

ORD record
ord-99f27fb9c8074337970edd32aff37eb5
Source dataset
uspto-grants-2008_08
Patent number
US07414055B2

Reaction notes

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