Chloroform → HCID 67350741, compound

HRID 1672788Notes

Reaction equation

HRID 1672788 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=3)[C:20]([NH:22][NH2:23])=[O:21])[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:27]=1.[CH:28]([N:31]=[C:32]=O)([CH3:30])[CH3:29].C(=O)(O)[O-].[Na+].C(Cl)(Cl)Cl>ClCCl>[CH:28]([NH:31][C:32]1[O:21][C:20]([C:19]2[CH:18]=[C:17]([N:14]3[CH2:13][C@H:12]4[N:8]([CH2:9][CH2:10][CH2:11]4)[C:7]4[N:27]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][C:6]=4[C:15]3=[O:16])[CH:26]=[CH:25][CH:24]=2)=[N:22][N:23]=1)([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 61277Isopropyl isocyanateHCID 516892Sodium BicarbonateHCID 67350136HCID 67350136, compound

Product 1

HCID 67350741HCID 67350741, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic hydrazide (300 mg, 0.780 mmol) obtained in Step 2 of Example 56 was dissolved in dichloromethane (16 mL), and the mixture was stirred at room temperature for 14 hours after adding isopropyl isocyanate (0.092 mL, 0.936 mmol). Thereafter, a saturated aqueous sodium bicarbonate solution and chloroform were added to the mixture to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Using the resulting residue, (S)-5-[3-(5-isopropylamino-1,3,4-oxadiazol-2-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (74.0 mg, 21%) was obtained in the same manner as in Step 3 of Example 52.

Workup

  1. customto separate the organic layer
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b72cf68a439849bfbf67ece7f87d8390
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

Loading…