Ammonium Chloride → (1S,2R)-4'-(4-Chlorophenyl)-2',3',9'-trimethylspiro[cyclo-propane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]-2-carboxamide

HRID 1772339Notes

Reaction equation

HRID 1772339 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[C:26]([NH:28]CC)=[O:27])[N:9]=2)=[CH:4][CH:3]=1.[Cl-].[NH4+]>>[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[C:26]([NH2:28])=[O:27])[N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 25517Ammonium ChlorideHCID 67951116(1S,2R)-4'-(4-Chlorophenyl)-N-ethyl-2',3',9'-trimethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]-2-carboxamide

Product 1

HCID 57404935(1S,2R)-4'-(4-Chlorophenyl)-2',3',9'-trimethylspiro[cyclo-propane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]-2-carboxamide

Procedure

A procedure analogous to that used for Compound 204 was followed, with the exception that ammonium chloride was used instead of ethylamine hydrochloride. LRMS (M+H)+: 412 m/z. 1H NMR (major conformer reported only) (400 MHz, DMSO-d6) δ 7.38-7.54 (m, 4H), 6.83 (br. s., 1H), 6.69 (br. s., 1H), 2.62 (s, 3H), 2.35 (s, 3H), 2.06 (dd, J=5.04, 8.93 Hz, 1H), 1.93 (t, J=6.20 Hz, 1H), 1.81 (t, J=7.80 Hz, 1H), 1.48 (s, 3H).

Sources & evidence

ORD record
ord-828aa9b26ba84b05a4ebfd900e99c87c
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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