Ammonia → HCID 59683534, compound

HRID 2389644Notes

Reaction equation

HRID 2389644 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:49])[CH:9]1[CH2:14][CH2:13][CH:12]([N:15]([CH2:30][C:31]2[CH:32]=[C:33]([C:39]3[CH:44]=[CH:43][N:42]=[C:41]([C:45]([O:47]C)=O)[CH:40]=3)[CH:34]=[CH:35][C:36]=2[O:37][CH3:38])[C:16]([C:18]2[S:22][C:21]3[C:23]([F:28])=[CH:24][CH:25]=[C:26]([F:27])[C:20]=3[C:19]=2[Cl:29])=[O:17])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH3:50]>O1CCOCC1>[C:45]([C:41]1[CH:40]=[C:39]([C:33]2[CH:34]=[CH:35][C:36]([O:37][CH3:38])=[C:31]([CH:32]=2)[CH2:30][N:15]([C:16]([C:18]2[S:22][C:21]3[C:23]([F:28])=[CH:24][CH:25]=[C:26]([F:27])[C:20]=3[C:19]=2[Cl:29])=[O:17])[CH:12]2[CH2:11][CH2:10][CH:9]([N:8]([CH3:49])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH2:14][CH2:13]2)[CH:44]=[CH:43][N:42]=1)(=[O:47])[NH2:50]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 59683538HCID 59683538, compound

Product 1

HCID 59683534HCID 59683534, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl ester 148 (50 mg, 0.07 mmol) in 1,4-dioxane (2 mL) is treated with conc. ammonia (1 mL) and the reaction stirred at RT 6 h. LC/MS at this juncture showed some residual starting material so more conc. ammonia (1 mL) is added and the reaction mixture heated 2 h at 40° C. LC/MS at this juncture showed the reaction is complete. The solvents are removed in vacuo to give the title compound.

Workup

  1. additionis added
  2. temperaturethe reaction mixture heated 2 h at 40° C
  3. customThe solvents are removed in vacuo

Sources & evidence

ORD record
ord-7399cdb8834e40d7bbfb05f0de2a83c6
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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