Dichloromethane → (S)-N-(quinuclidine-8-yl)-2-(2-methylpiperazin-1-yl)benzoxazole-4-carboxamide Dihydrochloride

HRID 249840Notes

Reaction equation

HRID 249840 reaction equation
[CH3:1][CH:2]1[N:7]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[O:27])[NH:18][CH:19]4[CH:24]5[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]5)[CH2:20]4)[C:11]=3[N:12]=2)[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:43]>>[ClH:43].[ClH:43].[N:21]12[CH2:20][CH:19]([NH:18][C:17]([C:13]3[CH:14]=[CH:15][CH:16]=[C:10]4[O:9][C:8]([N:7]5[CH2:6][CH2:5][NH:4][CH2:3][C@@H:2]5[CH3:1])=[N:12][C:11]=34)=[O:27])[CH:24]([CH2:23][CH2:22]1)[CH2:25][CH2:26]2

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66874421HCID 66874421, compound

Product 1

HCID 66874654(S)-N-(quinuclidine-8-yl)-2-(2-methylpiperazin-1-yl)benzoxazole-4-carboxamide Dihydrochloride

Procedure

To an ice-cold solution of tert-butyl 3-methyl-4-(4-(quinuclidine-8-ylcarbamoyl)benzoxazole-2-yl)piperazine-1-carboxylate. (90 mg, 0.19 mmol) in CH2Cl2 (5 mL) was added TFA(0.25 mL, 3.2 mmol). The reaction mixture was stirred at room temperature for 12 h, and then concentrated under reduced pressure. The resulting TFA salt was converted to (S—N-(quinuclidine-8-yl)-2-(2-methylpiperazin-1-yl)benzoxazole-4-carboxamide dihydrochloride following GP-D1. 1H NMR and MS consistent.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b5af2954dba04464ad1b0ef889d5d773
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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