Methanol → HCID 118294404, compound

HRID 2205180Notes

Reaction equation

HRID 2205180 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@:8]([CH2:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([CH:18]([F:20])[F:19])[O:7][C@H:6]1[N:30]1[CH:38]=[N:37][C:36]2[C:31]1=[N:32][CH:33]=[N:34][C:35]=2[NH:39]C(=O)C1C=CC=CC=1)(=O)C.CO>N>[NH2:39][C:35]1[N:34]=[CH:33][N:32]=[C:31]2[C:36]=1[N:37]=[CH:38][N:30]2[C@H:6]1[C@H:5]([OH:4])[C@H:9]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C@:8]([CH2:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([CH:18]([F:20])[F:19])[O:7]1

Participants

4

Reactant 2

HCID 887MethanolHCID 118294237HCID 118294237, compound

Product 1

HCID 118294404HCID 118294404, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of compound 25 (0.225 g, 0.35 mmol) in NH3.MeOH (40 mL) was stirred in a sealed tube at 65° C. for 16 hrs, warmed to 25° C. and stirred for 3 hrs. TLC showed the reaction was completed, the reaction solution was concentrated and the crude compound was purified by silica gel chromatography column [dichloromethan:methanol (30:1)] to give product 26 as an colorless oil (0.16 g, 92%).

Workup

  1. concentrationthe reaction solution was concentrated
  2. customthe crude compound was purified by silica gel chromatography column [dichloromethan:methanol (30:1)]

Sources & evidence

ORD record
ord-461eddf8ed904d7dacbb4e79b95c418a
Source dataset
uspto-grants-2016_06
Patent number
US09370569B2

Reaction notes

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