Hydrochloric Acid → HCID 86727568, compound

HRID 519166Notes

Reaction equation

C(OC([N:8]1[CH2:12][CH2:11][C:10]([NH:14][C:15]2[CH:16]=[C:17]3[C:26](=[CH:27][C:28]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[F:35])[O:25][CH2:24][C:23]2[N:18]3[CH:19]([CH3:37])[C:20](=[O:36])[NH:21][N:22]=2)([CH3:13])[CH2:9]1)=O)(C)(C)C.[ClH:38]>>[ClH:38].[F:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:28]1[CH:27]=[C:26]2[C:17]([N:18]3[C:23]([CH2:24][O:25]2)=[N:22][NH:21][C:20](=[O:36])[CH:19]3[CH3:37])=[CH:16][C:15]=1[NH:14][C:10]1([CH3:13])[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 86727566HCID 86727566, compound

Product 1

HCID 86727568HCID 86727568, compoundYield 87%

Procedure

A mixture of 3-[7-(2-fluoro-phenyl)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino]-3-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.008 g, 0.017 mmol) in HCl (4 M in EtOAc, 2 mL) was stirred at ambient temperature for 1 h. The solvent was removed in vacuo to give 7-(2-fluoro-phenyl)-4-methyl-6-(3-methyl-pyrrolidin-3-ylamino)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one hydrochloride acid (0.007 g, 87%) as a white solid. 1H NMR (400 MHz, methanol-d4) δ 7.53-7.42 (m, 1H), 7.41-7.34 (m, 1H), 7.34-7.29 (m, 1H), 7.29-7.22 (m, 1H), 6.89 (s, 1H), 6.70-6.64 (m, 1H), 4.97-4.93 (m, 1H), 4.64-4.57 (s, 2H), 3.60-3.45 (m, 1H), 3.38-3.34 (m, 2H), 3.18-3.07 (m, 1H), 2.20-2.06 (m, 1H), 2.04-1.92 (m, 1H), 1.56-1.47 (m, 3H), 1.39 (m, 3H). LC/MS (Table 1, Method 5) Rt=2.272 min; MS m/z: 410 [M+H]+.

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-d38c5c5f9a2142ce9b3cc79032373672
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115151B2

Reaction notes

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