Methylamine → HCID 67197631, compound

HRID 1948747Notes

Reaction equation

HRID 1948747 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:20])[CH:5]=[C:4]([CH3:27])[N:3]=1.[CH3:28][NH2:29]>C1COCC1>[CH3:28][NH:29][C:2]1[N:3]=[C:4]([CH3:27])[CH:5]=[C:6]([S:8][CH2:9][C:10]2[C:11]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:20])[N:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 87552357HCID 87552357, compound

Product 1

HCID 67197631HCID 67197631, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of Example 85 (100 mg, 0.29 mmol), THF (1 mL) and 2M methylamine in THF (5 mL) was heated in a microwave at 120° C. for 1 h. The solvent was removed in vacuo. Purification by preparative HPLC (Method 1) gave the title compound as a white solid (12 mg, 10%). δH (DMSO-d6) 8.52-8.55 (m, 1H), 7.82 (dd, J 8.3, 0.4 Hz, 1H), 7.68-7.72 (m, 2H), 7.59-7.64 (m, 1H), 7.45-7.55 (m, 4H), 6.95-7.05 (m, 1H), 6.30 (s, 1H), 4.55-4.65 (m, 2H), 2.68-2.75 (m, 6H), 2.11 (s, 3H). LCMS (ES+) 387.3 (M+H)+, RT 3.26 minutes (Method 3).

Workup

  1. customThe solvent was removed in vacuo
  2. customPurification by preparative HPLC (Method 1)

Sources & evidence

ORD record
ord-a6129e1354c6452fab663df056592555
Source dataset
uspto-grants-2013_03
Patent number
US08399483B2

Reaction notes

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