Morpholine → HCID 71571785, compound

HRID 1777795Notes

Reaction equation

Br[C:2]1[N:7]2[C:8](=[O:21])[N:9]([CH2:11][C@@H:12]3[CH2:14][C@H:13]3[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[O:25]1[CH2:26][CH2:27][N:22]([C:2]2[N:7]3[C:8](=[O:21])[N:9]([CH2:11][C@@H:12]4[CH2:14][C@H:13]4[C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=4)[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH2:23][CH2:24]1

Participants

Reactant 2

HCID 8083Morpholine

HCID 71571784HCID 71571784, compound

Product 1

HCID 71571785HCID 71571785, compoundYield 62.3%

Conditions

Temperature: 120 °C

Procedure

In a 1 mL microwave vial were placed 13-5 (22 mg, 0.064 mmol) and morpholine (1.00 g, 1.00 mL, 11.5 mmol). The vial was sealed and heated at 120° C. under microwave irradiation for 10 min. The reaction mixture was directly purified by reversed phase chromatography to give 14.0 mg (62%) of 13-6. 1H NMR δ (500 MHz, DMSO-d6): δ 8.44 (d, J=5.0 Hz, 1H), 7.81 (s, 1H), 7.36 (d, J=8.0 Hz, 1H), 7.28 (s, 1H), 7.01 (dd, J=9.3, 7.0 Hz, 1H), 6.72 (d, J=9.3 Hz, 1H), 5.75 (d, J=7.0 Hz, 1H), 3.90 (dd, J=6.9, 3.9 Hz, 2H), 3.74 (t, J=4.6 Hz, 4H), 3.12-3.03 (m, 4H), 2.25 (dt, J=8.5, 4.6 Hz, 1H), 1.84 (s, 1H), 1.23-1.15 (m, 2H). HRMS (ES) 352.1761 (M+H) found, 352.1768 required.

Workup

customThe vial was sealed
customThe reaction mixture was directly purified by reversed phase chromatography

Sources & evidence

ORD record: ord-05ea4bfc195a4e89a9c8b64a2fa9d516
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266881B2

Reaction notes

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