(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] → 6-(4-Chlorophenyl)-1-methylspiro[benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepine-4,1'-cyclopropane]

HRID 1772357Notes

Reaction equation

HRID 1772357 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=C(C)S[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.Cl[C:30]1C=CC(C2C3C=CC=CC=3NC(=O)C3(N=2)CC3)=C[CH:31]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[CH:19][CH:30]=[CH:31][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[C:10]3([CH2:24][CH2:25]3)[N:9]=2)=[CH:4][CH:3]=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 678182825-(4-Chlorophenyl)spiro[benzo[e][1,4]diazepine-3,1'-cyclopropan]-2(1H)-one

Product 1

HCID 574052686-(4-Chlorophenyl)-1-methylspiro[benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepine-4,1'-cyclopropane]

Procedure

A procedure analogous to that set forth for Compound 202 was followed, with the exception that 5-(4-chlorophenyl)spiro[benzo[e][1,4]diazepine-3,1′-cyclopropan]-2(1H)-one was used as starting material. LRMS (M+H)+: 335 m/z. 1H NMR (400 MHz, DMSO-d6) δ 7.74-7.79 (m, 2H), 7.46-7.58 (m, 5H), 7.32 (d, J=7.55 Hz, 1H), 2.58 (s, 3H), 1.67-1.77 (m, 1H), 1.34-1.44 (m, 1H), 0.67-0.83 (m, 2H).

Sources & evidence

ORD record
ord-edfa96d4eb1f4ddbb3076d16d6728455
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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