Sodium Bicarbonate → HCID 71599150, compound

HRID 2174580Notes

Reaction equation

O[C:2]1([C:23]2[O:24][C:25]3[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=3[C:27]=2[CH3:28])[CH2:7][CH2:6][N:5]([C:8](=[O:22])/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]3[C:18](=[N:19][CH:20]=2)[NH:17][C:16](=[O:21])[CH2:15][CH2:14]3)[CH2:4][CH2:3]1.C([O-])(O)=O.[Na+]>Cl>[CH3:28][C:27]1[C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=2[O:24][C:23]=1[C:2]1[CH2:7][CH2:6][N:5]([C:8](=[O:22])/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]3[C:18](=[N:19][CH:20]=2)[NH:17][C:16](=[O:21])[CH2:15][CH2:14]3)[CH2:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3d (50 mg, 0.11 mmol) in 10% HCl solution (5 ml) was stirred at 100° C. for 6 h. The progress of the reaction was monitored by TLC. After 6 h of stirring, the mixture was cooled to 0° C. and basified with NaHCO3 solution. The resultant solid was filtered, washed with water and dried under vacuum for 16 h. The crude compound was purified by column chromatography using a mixture of 1% methanol/chloroform as an eluent to get the desired compound-3 as a pale brown solid (15 mg, 33%). 1H NMR (400 MHz, DMSO-d6) δ 10.65 (s, 1H), 8.38 (s, 1H), 8.11 (d, J=16.7 Hz, 1H), 7.59 (d, J=7.3 Hz, 1H), 7.53-7.47 (m, 2H), 7.38-7.22 (m, 3H), 6.42-6.34 (m, 1H), 4.56-4.44 (m, 1H), 4.38-4.24 (m, 1H), 3.98-3.90 (m, 1H), 3.89-3.77 (m, 1H), 2.93 (t, J=7.5 Hz, 2H), 2.78-2.70 (m, 1H), 2.67-2.64 (m, 1H), 2.57-2.54 (m, 2H), 2.35 (s, 3H); MS (ES) m/e 414.1 (M+H)+.

Workup

filtrationThe resultant solid was filtered
washwashed with water
customdried under vacuum for 16 h
customThe crude compound was purified by column chromatography
additiona mixture of 1% methanol/chloroform as an eluent

Sources & evidence

ORD record: ord-a416fcc6ee7548e5bac88d9dcd836add
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062002B2

Reaction notes

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