Hydrochloric Acid → (S)-morpholine-3-carboxylic acid (2-phenyl-imidazo[2,1-b]thiazol-6-yl)-amide, hydrochloride

HRID 1811668Notes

Reaction equation

HRID 1811668 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][O:11][CH2:10][C@H:9]1[C:14](=[O:30])[NH:15][C:16]1[N:17]=[C:18]2[N:22]([CH:23]=1)[CH:21]=[C:20]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[S:19]2)=O)(C)(C)C.O1CCCC1.[ClH:36].[SiH](CC)(CC)CC>O1CCOCC1>[ClH:36].[C:24]1([C:20]2[S:19][C:18]3=[N:17][C:16]([NH:15][C:14]([C@@H:9]4[CH2:10][O:11][CH2:12][CH2:13][NH:8]4)=[O:30])=[CH:23][N:22]3[CH:21]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 12052TriethylsilaneHCID 67241216(S)-3-(2-phenyl-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 131730186(S)-morpholine-3-carboxylic acid (2-phenyl-imidazo[2,1-b]thiazol-6-yl)-amide, hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 15 (0.06 mmol) was added to a mixture of tetrahydrofuran (0.7 mL) and 4M HCl in dioxane (0.7 mL). Et3SiH (0.408 mmol) was added and the reaction mixture was stirred at room temperature for 4 hrs. The reaction mixture was concentrated under reduced pressure to give compound 16 as an orange solid in quantitative yield. MS (ESI, EI+) m/z=329.19 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-20a00ed0de384782936da7fd7000ae03
Source dataset
uspto-grants-2013_01
Patent number
US08362068B2

Reaction notes

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