Hydrochloric Acid → HCID 67298900, compound

HRID 1008972Notes

Reaction equation

HRID 1008972 reaction equation
[CH:1]1([C:7]2[C:8]3[S:29][C:28]([C:30]([O:32][CH3:33])=[O:31])=[CH:27][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[N:13]([CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])[C:12](=O)[CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B.CSC.Cl>C1COCC1.CO>[CH:1]1([C:7]2[C:8]3[S:29][C:28]([C:30]([O:32][CH3:33])=[O:31])=[CH:27][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[N:13]([CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])[CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 12423031(Dimethyl sulfide)trihydroboronHCID 67298736HCID 67298736, compound

Product 1

HCID 67298900HCID 67298900, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution (0.1 M) of methyl 12-cyclohexyl-5-[2-(dimethylamino)ethyl]-6-oxo-6,7-dihydro-5H-thieno[2′,3′:4,5]pyrrolo[1,2-d][1,4]benzodiazepine-10-carboxylate (from Example 7, Step 5) in THF was treated with borane-dimethylsulfide complex (2 M solution in THF, 20 eq.). The mixture was stirred at RT for 2 h then treated with HCl in methanol (1.25 M) and heated at 75° C. for 30 mins. The solvents were removed in vacuo and the residue taken into EtOAc and washed with saturated NaHCO3 solution and brine, dried over sodium sulfate and concentrated in vacuo to give the title compound as a solid. 1H-NMR (400 MHz, DMSO-d6, 300 K, δ) 7.99 (s, 1H), 7.40-7.36 (t, J 8, 1H), 7.29-7.27 (d, J 8, 1H), 7.23-7.21 (d, J 8, 1H), 7.14-7.10 (t, J 8, 1H), 4.17 (m, 2H), 3.82 (s, 3H), 3.43-3.39 (m, 2H), 3.20-3.17 (m, 2H), 2.70-2.67 (m, 1H), 2.32-2.23 (m, 2H), 2.01 (s, 6H), 1.81-1.23 (m, 10H). MS (ES+) m/z: 452 [M+H]+.

Workup

  1. temperatureheated at 75° C. for 30 mins
  2. customThe solvents were removed in vacuo
  3. washwashed with saturated NaHCO3 solution and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74ee6cbcb4124ef4bb295be4d616f193
Source dataset
uspto-grants-2011_07
Patent number
US07973026B2

Reaction notes

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