Acetic Acid → HCID 46844020, compound

HRID 1038342Notes

Reaction equation

C([O:9][C@H:10]1[C@:14]([F:16])([CH3:15])[C@H:13]([N:17]2[CH:25]=[N:24][C:23]3[C:18]2=[N:19][C:20]([NH2:27])=[N:21][C:22]=3Cl)[O:12][C@@H:11]1[CH2:28][O:29]C(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C[O-].[Na+].C[C:42](O)=[O:43]>CO>[NH2:27][C:20]1[N:19]=[C:18]2[C:23]([N:24]=[CH:25][N:17]2[C@@H:13]2[O:12][C@H:11]([CH2:28][OH:29])[C@@H:10]([OH:9])[C@:14]2([F:16])[CH3:15])=[C:22]([O:43][CH3:42])[N:21]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 4 (500 mg, 0.951 mmol) in MeOH (10 ml) was added NaOMe in MeOH (25%, 0.90 ml). The mixture was heated to 50° C. for 3 h. Then, it was neutralized with AcOH. It was concentrated and EtOAC (30 ml) was added. The insoluble solid was filtered off The filtrate was concentrated and purified by flash column chromatography on silica gel using 0 to 15% MeOH in CH2Cl2 as eluents. Compound 7 (203 mg, 68.3%) was obtained as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 8.17 (s, 1H), 6.61 (s, 2H), 6.05 (d, J=17.6 Hz, 1H), 5.67 (d, J=7.2 Hz, 1H), 5.25 (t, J=4.8 Hz, 1H), 4.18 (dt, J=25.6, 8.0 Hz, 1H), 3.96 (s, 3H), 3.91 (dm, J=9.2 Hz, 1H), 3.85 (ddd, J=2.0, 5.2, 12.8 Hz, 1H), 3.69 (ddd, J=2.8, 3.2, 12.0 Hz, 1H), 1.06 (d, J=22.8 Hz, 3H); tR=0.52 (99.1%); LRMS (ESI) [M+H]+ calculated for C12H17FN5O4 314.3, found 314.2.

Workup

concentrationIt was concentrated
additionEtOAC (30 ml) was added
filtrationThe insoluble solid was filtered off The filtrate
concentrationwas concentrated
custompurified by flash column chromatography on silica gel using 0 to 15% MeOH in CH2Cl2 as eluents

Sources & evidence

ORD record: ord-4b2c33a9860949a186d90071fd99fe82
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551973B2

Reaction notes

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