(R)-Solketal → (1R,2S)-4'-(4-chlorophenyl)-2-(methoxymethyl)-2',3',9'-trimethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]

HRID 1772343Notes

Reaction equation

HRID 1772343 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][O:27][CH3:28])[N:9]=2)=[CH:4][CH:3]=1.CC1(C)O[C@H](CO)CO1>>[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][C@@H:24]3[CH2:26][O:27][CH3:28])[N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 736056(R)-SolketalHCID 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]

Product 1

HCID 57404939(1R,2S)-4'-(4-chlorophenyl)-2-(methoxymethyl)-2',3',9'-trimethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]

Procedure

The above employed synthesis scheme was identical to that set forth for Compound 202, except that (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methanol was used as starting material and the indicated enantiomers were produced at each step. LRMS (M+H)+: 413 m/z. 1H NMR (two conformers detected in ˜1:1 ratio) (400 MHz, DMSO-d6) δ 7.38-7.56 (m, 4H), 3.82 (dd, J=7.32, 10.76 Hz, 0.5H), 3.71 (dd, J=6.87, 10.99 Hz, 0.5H), 3.39 (s, 1.5H), 3.21 (dd, J=6.41, 10.76 Hz, 0.5H), 3.04 (dd, J=7.44, 10.87 Hz, 0.5H), 2.96 (s, 1.5H), 2.60 (s, 3H), 2.39 (s, 1.5H), 2.38 (s, 1.5H), 2.16-2.26 (m, 0.5H), 2.05 (dd, J=5.26, 9.61 Hz, 0.5H), 1.58 (s, 1.5H), 1.54 (s, 1.5H), 1.43-1.52 (m, 0.5H), 1.33-1.39 (m, 0.5H), 1.03 (dd, J=5.26, 9.38 Hz, 0.5H), 0.60 (t, J=6.07 Hz, 0.5H).

Workup

  1. customsynthesis scheme
  2. customthe indicated enantiomers were produced at each step

Sources & evidence

ORD record
ord-dd5b79d0cab0455dba26f7f7d10a3a22
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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