Hydrochloric Acid → HCID 86723202, compound

HRID 1050319Notes

Reaction equation

HRID 1050319 reaction equation
[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([O:10][C@@H:11]3[CH2:28][N:14]4[C:15](=[O:27])[CH2:16][CH2:17][N:18](C(OC(C)(C)C)=O)[CH2:19][C@@H:13]4[CH2:12]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[ClH:29]>CO.ClCCl.O1CCOCC1>[ClH:29].[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([O:10][C@@H:11]3[CH2:28][N:14]4[C:15](=[O:27])[CH2:16][CH2:17][NH:18][CH2:19][C@@H:13]4[CH2:12]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86723201HCID 86723201, compound

Product 1

HCID 86723202HCID 86723202, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To tert-butyl (8S,9aS)-8-[(5-cyclopropylpyrazin-2-yl)oxy]-5-oxohexahydro-1H-pyrrolo[1,2-a][1,4]diazepine-2(3H)-carboxylate (254 mg, 0.654 mmol, Part C) in methanol/dichloromethane (1:1, 1 mL) was added 4 N HCl solution in dioxane (3 mL). The mixture was stirred at room temperature for three hours and then concentrated to give 212 mg (100% yield) of the title compound as a solid which was used without purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.82 (m, 2H), 0.96 (m, 2H), 2.10 (m, 2H), 2.66 (m, 1H), 3.10 (m, 3H), 3.40 (m, 2H), 3.65 (m, 2H), 4.22 (m, 1H), 4.40 (m, 1H), 5.38 (m, 1H), 8.15 (d, J=1 Hz, 1H), 8.19 (d, J=1 Hz, 1H), 9.38 (br s, 1H), 9.50 (br s, 1H); MS (ESI) m/z 289.0 (M+H)+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-2368c2e7b4894dec8012209e94bd65e5
Source dataset
uspto-grants-2016_07
Patent number
US09382258B2

Reaction notes

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