Hydrochloric Acid → HCID 86708909, compound

HRID 1522058Notes

Reaction equation

HRID 1522058 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12](=[O:29])[CH2:13][N:14]1[S:19](=[O:21])(=[O:20])[N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16][CH2:15]1)[CH2:8]2.[ClH:30]>C(Cl)Cl.O1CCOCC1>[ClH:30].[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12](=[O:29])[CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][NH:18][S:19]1(=[O:21])=[O:20])[CH2:8]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 70675029HCID 70675029, compound

Product 1

HCID 86708909HCID 86708909, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 6-(2-(adamantan-2-yl amino)-2-oxoethyl)-1,2,6-thiadiazinan-2-carboxylate 1,1-dioxide (150 mg, 0.351 mmol) in CH2Cl2 (5 mL), was added an excessive amount of 4 M HCl in 1.4-dioxane. The reaction mixture was agitated for 4 hr at room temperature and evaporated to give N-(adamantan-2-yl)-2-(1,1-dioxido-1,2,6-thiadiazinan-2-yl)acetamide hydrochloride (120 mg, 92%, white solid). 1H NMR (300 MHz, DMSO-d6): δ 7.06-7.57 (brd, 1H), 7.00 (t, J=6.9 Hz, 1H), 3.85-3.82 (m, 1H), 3.59 (s, 2H), 3.33-3.23 (m, 4H), 1.90-1.48 (m, 16H).

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-dc516ab6ab354776b2acb3f6aa94896d
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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