Methanol → HCID 178420054, compound

HRID 1678768Notes

Reaction equation

HRID 1678768 reaction equation
[NH:1]([C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:7]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:20]3[CH2:25][CH2:24][CH:23]([C:26]4[NH:30][C:29]([C:31]5[CH:36]=[N:35][CH:34]=[CH:33][N:32]=5)=[N:28][N:27]=4)[CH2:22][CH2:21]3)=[CH:15][CH:14]=1)=[N:8]2)[NH2:2].CO.[CH:45](OC)(OC)OC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:37]1([C:6]2[C:7]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[CH2:25][CH2:24][CH:23]([C:26]5[NH:30][C:29]([C:31]6[CH:36]=[N:35][CH:34]=[CH:33][N:32]=6)=[N:28][N:27]=5)[CH2:22][CH2:21]4)=[CH:15][CH:14]=3)=[N:8][C:9]3[CH:10]=[CH:11][N:12]4[CH:45]=[N:2][N:1]=[C:3]4[C:4]=3[CH:5]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 178514341HCID 178514341, compound

Product 1

HCID 178420054HCID 178420054, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 10-3 (0.5 g, 0.9 mMol) in 16 mL of 3:1 toluene:methanol was added trimethyl orthoformate (0.3 g, 2.7 mMol) and p-toluenesulfonic acid monohydrate (0.017 g, 0.09 mMol). The reaction was heated to 100° C. in a microwave reactor for 1 hour. After cooling to room temperature, the solvent was removed under reduced pressure. The product was purified on a C18 reverse phase HPLC to give 10-4 as a solid. Mass (M+1) calculated: 565.2571 observed: 565.2523

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed under reduced pressure
  3. customThe product was purified on a C18 reverse phase HPLC

Sources & evidence

ORD record
ord-a093beb43e414f3a99deacb9352392f1
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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