Chlorosuccinimide → HCID 67360062, compound

HRID 1668364Notes

Reaction equation

[C:1]([C:3]1[C:26]([F:27])=[CH:25][C:6]2[O:7][C:8]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:9]=3[C@H:10]3[C@H:15]([NH:16][C:17](=[O:19])[CH3:18])[CH2:14][CH2:13][CH2:12][N:11]3[C:5]=2[CH:4]=1)#[N:2].C1C(=O)N([Cl:35])C(=O)C1>>[Cl:35][C:4]1[C:5]2[N:11]3[CH2:12][CH2:13][CH2:14][C@@H:15]([NH:16][C:17](=[O:19])[CH3:18])[C@@H:10]3[C:9]3[C:20]([F:24])=[CH:21][CH:22]=[CH:23][C:8]=3[O:7][C:6]=2[CH:25]=[C:26]([F:27])[C:3]=1[C:1]#[N:2]

Participants

Reactant 2

HCID 31398Chlorosuccinimide

HCID 67359732HCID 67359732, compound

Product 1

HCID 67360062HCID 67360062, compoundYield 62.7%

Procedure

Preparation analogous to Example 3 from (−)-(cis)-N-(7-cyano-8,14-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)acetamide (0.277 g, 0.75 mmol) and NCS (0.10 g, 0.75 mmol). The crude compound was purified by HPLC to give the title compound (0.19 g, 62%). 1H-NMR (600 MHz, DMSO) 1.46-1.57 (m, 4H), 1.64 (m, 1H), 1.72 (m, 1H), 1.92 (m, 1H), 3.27 (m, 1H), 3.53 ( m, 1H), 4.31 (d, J=11.6, 1H), 4.38 (m, 1H), 7.05 (m, 1H), 7.11 (d, J=8.7, 1H), 7.33 (m, 1H), 7.64 (d, J=9.8, 1H), 7.81 (br-d, J=9.8, 1H). e.e.=100%, Rf=17.8 min. (chiralpak OD-H 25*0.46 cm, heptane:ethanol=9:1). (MIM)=403. [α]D20=−207° (c=1.0025, THF).

Workup

customThe crude compound was purified by HPLC

Sources & evidence

ORD record: ord-1a32fce5244b4d06a7cc2a0a3c34ee75
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989442B2

Reaction notes

Loading…