HCID 178488095, compound → HCID 178488094, compound

HRID 1274154Notes

Reaction equation

C([O:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[NH:24][C:23]4[CH:25]=[CH:26][C:27]([O:29][CH3:30])=[CH:28][C:22]=4[N:21]=3)[CH2:16][CH2:15]2)=[CH:9][CH:8]=1)(C)(C)C>C(O)(C(F)(F)F)=O>[CH3:30][O:29][C:27]1[CH:26]=[CH:25][C:23]2[NH:24][C:20]([N:17]3[CH2:18][CH2:19][CH:14]([NH:13][C:10]4[CH:11]=[CH:12][C:7]([C:6]([OH:31])=[O:5])=[CH:8][CH:9]=4)[CH2:15][CH2:16]3)=[N:21][C:22]=2[CH:28]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of (12) (0.03 g, 0.071 mmol) in TFA (5 mL) was capped with a drying tube and stirred at 25° C. for 12 h. The reaction mixture was then concentrated to a light brown oily residue (0.033 g, 97.5%); 1H NMR (DMSO) δ 13.00 (br s, 1H), 7.68 (d, 2H, J=8.6), 7.30 (d, 1H, J=8.7), 6.92 (d, 1H, J=2.2), 6.85 (dd, 1H, J=8.0, 2.3), 3.99 (d, 2H, J=13.3), 3.78 (s, 3H), 3.70 (m, 1H), 3.46 (t, 2H, J=11.2), 2.09 (d, 2H, J=10.7), 1.56 (m, 2H); 13C NMR (DMSO) δ 167.4, 156.2, 151.3, 150.0, 131.2, 131.0, 124.0, 117.1, 111.9, 111.3, 110.3, 96.6, 55.7, 47.3, 45.4, 30.2; HRMS (FAB) m/z 367.1777 (M+H)+ (C20H22N4O3 requires 367.1765); Anal. (C20H22N4O3 ·1CF3COOH·3/4H2O) C, H, N.

Workup

concentrationThe reaction mixture was then concentrated to a light brown oily residue (0.033 g, 97.5%)

Sources & evidence

ORD record: ord-4a1dbc181d88419f83eac3ee75b9befa
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156758

Reaction notes

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