(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] → Racemic 4'-(4-chlorophenyl)-2,2',3',9'-tetramethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]

HRID 1772355Notes

Reaction equation

HRID 1772355 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[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]3[CH2:26]OC)[N:9]=2)=[CH:4][CH:3]=1.ClC1C=CC(C2C3C(C)=C(C)SC=3NC(=O)C3(CC3C)N=2)=CC=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[C:10]3([CH2:25][CH:24]3[CH3:26])[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 137119440Racemic (1S,2R)-5'-(4-chlorophenyl)-2,6',7'-trimethylspiro[cyclopropane-1,3'-thieno[2,3-e][1,4]diazepin]-2'(1'H)-one

Product 1

HCID 76524868Racemic 4'-(4-chlorophenyl)-2,2',3',9'-tetramethylspiro[cyclopropane-1,6'-thieno[3,2-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 racemic (1S,2R)-5′-(4-chlorophenyl)-2,6′,7′-trimethylspiro[cyclopropane-1,3′-thieno[2,3-e][1,4]diazepin]-2′(1′H)-one was used as starting material. LRMS (M+H)+: 383 m/z. 1H NMR (400 MHz, DMSO-d6) δ 7.50 (s, 4H), 2.59 (s, 3H), 2.39 (s, 3H), 1.96-2.02 (m, 1H), 1.58 (s, 3H), 1.39 (d, J=6.18 Hz, 1H), 1.04 (d, J=5.95 Hz, 1H), 0.79 (d, J=5.49 Hz, 3H).

Sources & evidence

ORD record
ord-74ac13e915174a6cb83136f3e81e3247
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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