HCID 86727506, compound → HCID 86727507, compound

HRID 519122Notes

Reaction equation

HRID 519122 reaction equation
C(OC([N:8]1[CH2:11][C:10]([C@@H:13]([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[C@H:19]([CH3:37])[C:20](=[O:36])[NH:21][N:22]=2)[CH3:14])([CH3:12])[CH2:9]1)=O)(C)(C)C>Cl>[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])[C@H:19]3[CH3:37])=[CH:16][C:15]=1[C@H:13]([C:10]1([CH3:12])[CH2:11][NH:8][CH2:9]1)[CH3:14]

Participants

3

Reactant 1

HCID 86727506HCID 86727506, compound

Product 1

HCID 86727507HCID 86727507, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3-{(R)-1-[(R)-7-(2-fluoro-phenyl)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-ethyl}-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.073 g, 0.144 mmol) in HCl (4M in EtOAc, 1 mL) was stirred at ambient temperature for 1 h. The reaction mixture was concentrated in vacuo to give (R)-7-(2-fluoro-phenyl)-4-methyl-6-[(R)-1-(3-methyl-azetidin-3-yl)-ethyl]-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.06 g, 100%), which was used directly in the next step without further purification. 1H NMR (CD3OD, 400 MHz): δ 7.45 (m, 1H), 7.16-7.34 (m, 3H), 6.90-6.96 (m, 1H), 6.86 (s, 1H), 4.92-4.98 (m, 1H), 4.57-4.68 (m, 2H), 4.24 (m, 1H), 3.69-3.76 (m, 1H), 3.46-3.55 (m, 1H), 3.38 (m, 1H), 2.97 (m, 1H), 1.36-1.51 (m, 6H), 1.20-1.27 (m, 3H). LC/MS (Table 1, Method 25) Rt=0.673 min; MS (ESI): m/z 409 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f9ccccc20c1e496fa87e309cf2277592
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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