Triethylamine → HCID 86594475, compound

HRID 392900Notes

Reaction equation

C(N(CC)CC)C.[CH3:8][NH:9][C:10]([C@@H:12]1[C@@H:16]([N:17]=[N+:18]=[N-:19])[C@@H:15]([OH:20])[C@H:14]([N:21]2[CH:29]=[N:28][C:27]3[C:22]2=[N:23][CH:24]=[N:25][C:26]=3Cl)[O:13]1)=[O:11].[C:31]([O:35][C:36](=[O:48])[CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][C:40]=1[CH2:46][NH2:47])([CH3:34])([CH3:33])[CH3:32]>C(O)C>[C:31]([O:35][C:36](=[O:48])[CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][C:40]=1[CH2:46][NH:47][C:26]1[N:25]=[CH:24][N:23]=[C:22]2[C:27]=1[N:28]=[CH:29][N:21]2[C@H:14]1[C@H:15]([OH:20])[C@H:16]([N:17]=[N+:18]=[N-:19])[C@@H:12]([C:10](=[O:11])[NH:9][CH3:8])[O:13]1)([CH3:34])([CH3:32])[CH3:33]

Participants

Conditions

Temperature: 70 °C

Procedure

Triethyl amine (0.3 mL, 2.1 mmol) was added to a solution of (2S,3S,4R,5R)3-azido-5-(6-chloro-purin-9-yl)-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide (302 mg, 0.9 mmol) and 2-aminomethyl-4-chloro-phenoxy acetic acid tert-butyl ester (290 mg, 1.07 mmol) in ethanol at ambient temperature. The reaction was heated to 70° C. for 2.5 hours, cooled, and the resultant solid was washed with cold ethanol, and dried to afford 420 mg (81%) of the title compound as a colorless solid. Alternatively, the product could be purified by flash chromatography (2-5% methanol/dichloromethane). MS 574 (M+H)+. 1H NMR (400 MHz, CD3OD) δ 8.28 (bs, 1H); 8.24 (s, 1H); 7.32 (bs, 1H); 7.18 (dd, 1H, J=8.9, 2.6 Hz); 6.92 (d, 1H, J=8.9 Hz); 5.95 (d, 1H, J=7.1 Hz); 5.03 (dd, 1H, J=7.1, 4.9 Hz); 4.82 (bs, 2H); 4.83 (s, 2H); 4.39 (m, 2H); 3.0 (s, 1H); 2.8 (s, 3H); 1.4 (s, 9H).

Workup

temperaturecooled
washthe resultant solid was washed with cold ethanol
customdried

Sources & evidence

ORD record: ord-9a2af62188aa4d518ac4821b3059ae61
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06803457B1

Reaction notes

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