Serinol → HCID 178508209, compound

HRID 968236Notes

Reaction equation

Br[C:2]1[N:10]=[C:9]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=2[F:20])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([NH:21]C(=O)OCC)[NH:6]2.[NH2:27][CH:28]([CH2:31][OH:32])[CH2:29][OH:30].C(N(C(C)C)CC)(C)C>CN1C(=O)CCC1>[NH2:21][C:5]1[NH:6][C:7]2[C:3]([N:4]=1)=[C:2]([NH:27][CH:28]([CH2:31][OH:32])[CH2:29][OH:30])[N:10]=[C:9]([S:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[F:20])[N:8]=2

Participants

Conditions

Temperature: 150 °C

Procedure

The product of example 5, step (e) (40 mg) was dissolved in NMP and 2-amino-1,3-propanediol (49.2 mg) and diisopropylethylamine (31 μl) base was added and the solution was heated at 150° C. for 36 hr. The reaction mixture was then evaporated to a residue that was purified by preparative HPLC to yield the titled compound as a pale yellow solid (9.5 mg).

Workup

customThe reaction mixture was then evaporated to a residue that
customwas purified by preparative HPLC

Sources & evidence

ORD record: ord-683335363d7e4d3d93e517588d3d738e
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06958344B2

Reaction notes

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