4-Fluorobenzylamine → HCID 54697521, compound

HRID 1453868Notes

Reaction equation

C([O:8][C:9]1[C:10]([C:20]([OH:22])=O)=[N:11][N:12]2[CH2:18][CH2:17][CH2:16][NH:15][C:14](=[O:19])[C:13]=12)C1C=CC=CC=1.[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>>[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:29][C:20]([C:10]2[C:9]([OH:8])=[C:13]3[C:14](=[O:19])[NH:15][CH2:16][CH2:17][CH2:18][N:12]3[N:11]=2)=[O:22])=[CH:26][CH:25]=1

Participants

Reactant 2

HCID 673264-Fluorobenzylamine

HCID 689526853-Benzyloxy-4-oxo-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-2-carboxylic acid

Product 1

HCID 54697521HCID 54697521, compound

Procedure

The title compound was prepared from 3-benzyloxy-4-oxo-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-2-carboxylic acid using a procedure similar to that found in Example 13, Step 3, except that 4-fluorobenzylamine was used in place of 4-fluoro-N-methylbenzylamine and the reaction time totaled 10 minutes. Purification by reverse phase chromatography was not necessary. 1H NMR (400 MHz, CDCl3) δ 7.26-7.22 (m, 7H), 7.01-6.96 (m, 2H), 6.15 (br s, 1H), 5.30 (s, 2H), 4.57-4.55 (d, 2H), 4.46-4.43 (t, 2H), 3.16-3.11 (m, 2H), 2.20-2.13 (dt, 2H); ES MS (M+1)=409.

Workup

customPurification by reverse phase chromatography

Sources & evidence

ORD record: ord-de49faa62e8b49629974f972953c4f78
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07476666B2

Reaction notes

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