HCID 57654653, compound → HCID 57654650, compound

HRID 1175129Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]([Cl:19])[CH:17]=3)[CH2:12][CH2:11][C:10]=12)=[O:5])[CH3:2].O(C(C)(C)C)[Li].[C:26]([O:30][C:31]([N:33]1[CH2:36][C:35]([NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])([CH2:37]OS(C)(=O)=O)[CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:37][C:35]2([NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:34][N:33]([C:31]([O:30][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:32])[CH2:36]2)[N:8]=[C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]([Cl:19])[CH:17]=3)[CH2:12][CH2:11][C:10]=12)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

8-Chloro-4,5-dihydro-2H-1,2,7-triaza-cyclopenta[a]naphthalene-3-carboxylic acid ethyl ester (320 mg; 1.15 mmol) in DMF (4 ml) is treated at 5° C. with LiOtBu (1N in THF; 1.16 ml; 1.16 m mol) for 5 minutes. 3-tert-butoxycarbonylamino-3-methanesulfonyloxymethyl-azetidine-1-carboxylic acid tert-butyl ester (0.32 mg; 1.15 mmol) is added and the mixture heated to 90° C. for 30 minutes. The reaction mixture is poured on brine and extracted with TBME three times. The combined organic phases are dried over Na2SO4, evaporated to dryness and yield the title compound as colorless crystals. 1H-NMR (400 MHz; DMSO-d6: 8.38 (s, 1H); 7.65 (s, 1H); 7.42 (bs, 1H); 5.00 (bs, 2H); 4.34 (q, 2H); 4.03 (bd, 2H); 3.79 (m, 2H); 3.00 (m, 2H); 2.95 (m, 2H); 1.40 (s, 18H); 1.36 (t, 3H). MS (m/z) ES+: 562 (MH+).

Workup

additionThe reaction mixture is poured on brine
extractionextracted with TBME three times
dry with materialThe combined organic phases are dried over Na2SO4
customevaporated to dryness

Sources & evidence

ORD record: ord-a3114a6d24574eb4bd05c95c22fe752e
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838674B2

Reaction notes

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