Thiophosgene → HCID 59618809, compound

HRID 1691454Notes

Reaction equation

HRID 1691454 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([C:25]([NH:27][NH2:28])=[O:26])[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:29]=[C:30]([C:33]([F:36])([F:35])[F:34])[CH:31]=[CH:32][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:37](Cl)(Cl)=[S:38]>C1COCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([C:25]4[O:26][C:37](=[S:38])[NH:28][N:27]=4)[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:29]=[C:30]([C:33]([F:35])([F:36])[F:34])[CH:31]=[CH:32][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 669016526-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carbohydrazide2×

Product 1

HCID 59618809HCID 59618809, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carbohydrazide (intermediate 57, 0.040 g, 0.0771 mmol) in THF (0.6 mL) at −78° C was added thiophosgene (0.010 mL). After stirring for 1 h at −78° C, the reaction was quenched with saturated aqueous NaHCO3 and the product was extracted with EtOAc. The combined extracts were washed with brine, dried (MgSO4) and concentrated. The residue was purified by SiO2 column chromatography, eluting with mixtures of EtOAc in hexanes, to provide the title compound. LC/MS: m/e 562.1 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 8.22 (1H, d, J=1.8 Hz), 7.82 (1H, dd, J=8.4, 2.0 Hz), 7.65 (1H, d, J=7.4 Hz), 7.17 (1H, d, J=7.5 Hz), 7.13-7.16 (2H, m), 7.10 (1H, br s), 6.97-6.99 (2H, m), 6.88 (1H, d, J=8.5 Hz), 4.70-4.95 (2H, br), 1.25 (9H, s).

Workup

  1. customthe reaction was quenched with saturated aqueous NaHCO3
  2. extractionthe product was extracted with EtOAc
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by SiO2 column chromatography
  7. washeluting with mixtures of EtOAc in hexanes

Sources & evidence

ORD record
ord-8dabc6f275584f6a9d351e1b0cc2506b
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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