(2'R,9S)-7-(4-chlorophenyl)-2'-(methoxymethyl)-4,5,13-trimethylspiro[3-thia-1,8,11,12-tetrazatricyclo[8.3.0.02,6]trideca-2(6),4,7,10,12-pentaene-9,1'-cyclopropane] → 4'-(4-Chlorophenyl)-3',9'-dimethylspiro[cyclopropane-1,6'-isothiazolo[4,5-f][1,2,4]triazolo[4,3-a][1,4]diazepine]

HRID 1772350Notes

Reaction equation

HRID 1772350 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15](C)=[C:16](C)[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[C@@:10]3([CH2:25][C@H:24]3COC)[N:9]=2)=[CH:4][CH:3]=1.ClC1C=CC(C2C3C(C)=NSC=3[NH:39]C(=O)C3(CC3)N=2)=CC=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:14]3[C:15]([CH3:16])=[N:39][S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[C:10]3([CH2:25][CH2:24]3)[N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 57345408(2'R,9S)-7-(4-chlorophenyl)-2'-(methoxymethyl)-4,5,13-trimethylspiro[3-thia-1,8,11,12-tetrazatricyclo[8.3.0.02,6]trideca-2(6),4,7,10,12-pentaene-9,1'-cyclopropane]HCID 1363380654'-(4-chlorophenyl)-3'-methylspiro[cyclopropane-1,6'-isothiazolo[5,4-e][1,4]diazepin]-7'(8'H)-one

Product 1

HCID 574051074'-(4-Chlorophenyl)-3',9'-dimethylspiro[cyclopropane-1,6'-isothiazolo[4,5-f][1,2,4]triazolo[4,3-a][1,4]diazepine]

Procedure

A procedure analogous to that set forth for Compound 202 was followed, with the exception that 4′-(4-chlorophenyl)-3′-methylspiro[cyclopropane-1,6′-isothiazolo[5,4-e][1,4]diazepin]-7′(8′H)-one was used as starting material. LRMS (M+H)+: 356 m/z. 1H NMR (400 MHz, DMSO-d6) δ 7.25-7.65 (m, 4H), 2.62 (br. s., 3H), 1.91 (s, 3H), 1.85-1.89 (m, 2H), 1.78-1.82 (m, 2H).

Sources & evidence

ORD record
ord-4e59e50b99a84de191c404ebfe739108
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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