Ammonia → HCID 140043493, compound

HRID 723102Notes

Reaction equation

HRID 723102 reaction equation
[C:1]([O:5][C:6](=[O:43])[NH:7][C:8]([C:10]1[S:11][C:12]([S:41][CH3:42])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=S)=[CH:26][C:25]=3[CH3:40])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].[NH3:44]>CO.[Hg]=O>[C:1]([O:5][C:6](=[O:43])[NH:7][C:8]([C:10]1[S:11][C:12]([S:41][CH3:42])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH2:44])=[N:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:26][C:25]=3[CH3:40])[CH:21]=[CH:22][CH:23]=2)(=[O:16])=[O:17])[CH:14]=1)=[NH:9])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 145857629HCID 145857629, compound

Product 1

HCID 140043493HCID 140043493, compound

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalyst2×HCID 887MethanolSolvent

Procedure

({4-[4′-(3-Hexyl-thioureido)-2′-methyl-biphenyl-3-sulfonyl]-5-methylsulfanyl-thiophen-2-yl}-imino-methyl)-carbamic acid tert-butyl ester (33 mg, 0.14 mmol. Example 136: step a) was dissolved into ammonia in methanol (2.0 M, 4 mL). To this was added mercury(II) oxide (33.9 mg, 0.16 mmol) and the reaction stirred at RT for 2 hours. Additional mercury(II) oxide (154 mg, 0.08 mmol) was added and the reaction was heated to 40° C. overnight. The reaction was filtered with 0.2 μM disk and washed with EtOAc followed by removal of solvents in vacuo that yielded the title compound which was used without further purification (30 mg). ESI-MS (m/z): Calcd. for C31H41N5O4S3: 644.2 (M+1); found: 644.1.

Workup

  1. temperaturethe reaction was heated to 40° C. overnight
  2. filtrationThe reaction was filtered with 0.2 μM disk
  3. washwashed with EtOAc
  4. customfollowed by removal of solvents in vacuo

Sources & evidence

ORD record
ord-fd1c52e8e9f34f17802041747b08cdb1
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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