Potassium Carbonate → HCID 86705400, compound

HRID 926132Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:7][N:6]([CH2:8][C:9]2[CH:18]=[N:17][C:16]3[NH:15][C:14](=[O:19])[N:13]4[N:20]=[CH:21][N:22]=[C:12]4[C:11]=3[CH:10]=2)[CH2:5][C@@H:4]([CH3:23])[O:3]1.[F:24][C:25]([F:36])([F:35])[O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][C@H:2]1[CH2:7][N:6]([CH2:8][C:9]2[CH:18]=[N:17][C:16]3[N:15]([CH2:31][C:30]4[CH:33]=[CH:34][C:27]([O:26][C:25]([F:24])([F:35])[F:36])=[CH:28][CH:29]=4)[C:14](=[O:19])[N:13]4[N:20]=[CH:21][N:22]=[C:12]4[C:11]=3[CH:10]=2)[CH2:5][C@@H:4]([CH3:23])[O:3]1

Participants

Conditions

Temperature: 55 °C

Procedure

To a mixture of 9-(((2S,6R)-2,6-dimethylmorpholino)methyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (50 mg, 0.16 mmol) and 4-(trifluoromethoxy)benzyl bromide (49 mg, 0.19 mmol) in DMF (2 mL) was added potassium carbonate (44 mg, 0.32 mmol). The resulting mixture was heated at 55° C. overnight. The crude mixture was filtered then purified directly (HPLC, 10-70% ACN-water) to afford the title compound (58 mg, 61%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 1.14 (d, J=6.15 Hz, 6H), 2.63-2.85 (m, 2H), 3.26-3.45 (m, 2H), 3.72-3.86 (m, 2H), 4.40-4.62 (m, 2H), 5.70 (s, 2H), 7.32 (d, J=8.28 Hz, 2H), 7.59 (d, J=8.66 Hz, 2H), 8.69 (s, 1H), 8.84 (s, 1H), 8.89 (br s, 1H). [M+H]=489.2.

Workup

filtrationThe crude mixture was filtered
customthen purified directly (HPLC, 10-70% ACN-water)

Sources & evidence

ORD record: ord-ddda405e51f44a01bd364d8990b2cbca
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284335B2

Reaction notes

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