Hydrochloric Acid → HCID 86727501, compound

HRID 519118Notes

Reaction equation

HRID 519118 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[CH:29]([CH3:31])[CH3:30])[O:25][CH2:24][C:23]2[N:18]3[C@H:19]([CH3:33])[C:20](=[O:32])[NH:21][N:22]=2)[CH3:14])([CH3:12])[CH2:9]1)=O)(C)(C)C.[ClH:34]>>[ClH:34].[CH:29]([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:32])[C@H:19]3[CH3:33])=[CH:16][C:15]=1[C@H:13]([C:10]1([CH3:12])[CH2:9][NH:8][CH2:11]1)[CH3:14])([CH3:30])[CH3:31]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86727500HCID 86727500, compound

Product 1

HCID 86727501HCID 86727501, compoundYield 44%

Procedure

A solution of 3-[(R)-1-((R)-7-isopropyl-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 (0.0736 g, 0.162 mmol) in HCl (4M in EtOAc, 0.8 mL) was stirred for 1.5 h at ambient temperature. The reaction mixture was concentrated in vacuo and the residue was purified by prep-HPLC (Table 3, Method 27) to give (R)-7-isopropyl-4-methyl-6-[(R)-1-(3-methyl-azetidin-3-yl)-ethyl]-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one hydrochloric acid (0.026 g, 44%) as a solid. 1H NMR (CD3OD-d4, 400 MHz): δ 7.01 (s, 1H), 6.83 (s, 1H), 4.87-4.82 (m, 1H), 4.60 (s, 2H), 4.16 (d, J=10.8 Hz, 1H), 4.02 (d, J=10.8 Hz, 1H), 3.64 (d, J=10.8 Hz, 1H), 3.55 (d, J=10.8 Hz, 1H), 3.42-3.37 (m, 1H), 3.18-3.11 (m, 1H), 1.52 (s, 3H), 1.45 (d, J=6.8 Hz, 3H), 1.38 (d, J=6.8 Hz, 3H), 1.30 (d, J=6.8 Hz, 3H), 1.16 (d, J=6.8 Hz, 3H). LC/MS (Table 1, Method 5) Rt=2.401 min.; MS m/z: 357 [M+H]+. SFC (Table 1, Method 26) Rt=7.575 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by prep-HPLC (Table 3, Method 27)

Sources & evidence

ORD record
ord-d00f99bc259d43898ca89d106871bb52
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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