(3S)-(-)-3-(Dimethylamino)pyrrolidine → HCID 86700432, compound

HRID 879622Notes

Reaction equation

HRID 879622 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:26]([CH3:27])=[CH:25][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=3)[S:17][C:13]=2[C:12]=1[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:35][N:36]([CH3:42])[C@H:37]1[CH2:41][CH2:40][NH:39][CH2:38]1>O1CCOCC1>[C:1]([O:5][C@@H:6]([C:11]1[C:26]([CH3:27])=[CH:25][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:39]4[CH2:40][CH2:41][C@H:37]([N:36]([CH3:42])[CH3:35])[CH2:38]4)[N:19]=3)[S:17][C:13]=2[C:12]=1[C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)[C:7]([O:9][CH3:10])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 86700414(S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

Product 1

HCID 86700432HCID 86700432, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (40 mg, 0.08 mmol) in dioxane (1 mL) was added (S)—N,N-dimethylpyrrolidin-3-amine (89 mg, 0.78 mmol) at room temperature. The reaction mixture was allowed to stir for an additional 30 minutes and then concentrated in vacuo to provide the desired product. LCMS-ESI+: calc'd for C31H37ClN5O3S: 594.2 (M+H+); Found: 594.4 (M+H+).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db0280f83cde435eb97c3d9d6058f077
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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