Hydrochloric Acid → HCID 70981542, compound

HRID 1749081Notes

Reaction equation

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

Participants

Reactant 2

HCID 313Hydrochloric Acid2×

HCID 70979656HCID 70979656, compound

Product 1

HCID 70981542HCID 70981542, compoundYield 80.7%

Procedure

{(S)-1-[1-(4-Chloro-phenyl)-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-ylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (23 mg) was treated with HCl, according to General procedure 3 (HCl deprotection), to give the title compound (8 mg). 1H NMR (400 MHz, DMSO-d6): 11.10 (1H, s), 9.20 (1H, br), 8.94 (1H, br), 7.71-7.59 (3H, m), 7.47-7.38 (2H, m), 6.86 (1H, d), 5.03 (2H, s), 4.01-3.92 (1H, m), 2.58-2.53 (3H, m), 1.47 (3H, d). MS: [M+H]+ 361.

Sources & evidence

ORD record: ord-009d9a2b295b48e59f9e213a6c85a3ba
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09155743B2

Reaction notes

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