3-Oxotetrahydrofuran → HCID 66547142, compound

HRID 403268Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C@:8]2([CH3:17])[C@@H:14]([F:15])[CH2:13][O:12][CH2:11][C:10]([NH2:16])=[N:9]2)[CH:7]=1.[O:19]1[CH2:23][CH2:22][C:21](=O)[CH2:20]1>>[F:15][C@H:14]1[CH2:13][O:12][CH2:11][C:10]([NH2:16])=[N:9][C@@:8]1([C:6]1[CH:7]=[C:2]([NH:1][CH:21]2[CH2:22][CH2:23][O:19][CH2:20]2)[CH:3]=[CH:4][C:5]=1[F:18])[CH3:17]

Participants

Reactant 2

HCID 5293923-Oxotetrahydrofuran

HCID 58562930HCID 58562930, compound

Product 1

HCID 66547142HCID 66547142, compoundYield 44.7%

Procedure

In an analogous manner as described for example 1 the reductive amination of (5R,6R)-5-(5-amino-2-fluoro-phenyl)-6-fluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-ylamine (intermediate A10B) (20 mg, 78.4 μmol) and dihydrofuran-3(2H)-one (3-oxotetrahydrofuran) (CAS [22929-52-8]) (7.42 mg, 6.67 μl, 86.2 μmol) yielded the title compound (11.4 mg, 44.7%) as a colorless solid. MS (ISP): m/z=326.3 [M+H]+.

Sources & evidence

ORD record: ord-7e01c6e1b0784f03a04cf688cbddf24c
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748418B2

Reaction notes

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