Methylamine → HCID 68355384, compound

HRID 1498486Notes

Reaction equation

HRID 1498486 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[N:11]([CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21](OS(C(F)(F)F)(=O)=O)[N:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[CH3:31][NH2:32].C1COCC1>CN1C(=O)CCC1.O>[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[C:16]4[CH:19]=[N:20][C:21]([NH:32][CH3:31])=[CH:22][C:15]=4[O:14][CH2:13][CH2:12][N:11]3[CH:10]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 582049872-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl trifluoromethanesulfonate

Product 1

HCID 68355384HCID 68355384, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of trifluoro-methanesulfonic acid 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-yl ester (100 mg, 0.23 mmol) in NMP was treated with 2M methylamine in THF (1.8 mL, 0.9 mmol) and heated at 85° C. for 20 h then diluted with water and stirred for 4 h. The precipitate was collected by filtration and dried in vacuo to give 416 as a white solid (19.5 mg, 28%). LCMS: RT=2.26 min, [M+H]+=326. 1H NMR 400 MHz (DMSO-d6) δ: 9.02 (1 H, s), 7.88 (1 H, s), 7.80 (1 H, s), 6.70 (1 H, br, m), 5.95 (1 H, s), 5.91-5.90 (1 H, m), 4.47 (4 H, q, J=6.12 Hz), 2.78 (3 H, d, J=4.86 Hz), 1.47 (6 H, d, J=6.60 Hz)

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-84920c2a01094bf3933926f5ce3f2d63
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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