Hydrochloric Acid → HCID 86727195, compound

HRID 579374Notes

Reaction equation

HRID 579374 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[C:13]1[S:17][C:16]([N:18]2[CH2:22][C@H:21]3[CH2:23][N:24](C(OC(C)(C)C)=O)[CH2:25][C@H:20]3[CH2:19]2)=[N:15][N:14]=1.Cl>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[C:13]1[S:17][C:16]([N:18]2[CH2:19][C@@H:20]3[C@@H:21]([CH2:23][NH:24][CH2:25]3)[CH2:22]2)=[N:15][N:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86727197HCID 86727197, compound

Product 1

HCID 86727195HCID 86727195, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of (3aR,6aS)-tert-butyl 5-(5-(2-chloro-4-(1H-pyrazol-4-yl)phenyl)-1,3,4-thiadiazol-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (10 mg, 0.021 mmol) in 1,4-dioxane (2 mL) was treated with 4M HCl in dioxane (1 mL) and stirred at room temperature for 3 h. The reaction mixture was concentrated in vacuo to give the title compound (2 mg, MS: 373.1 [M+H+], LCMS Rt=0.44 min (LCMS method D); 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.99 (br. s., 2H), 7.92 (d, J=8.59 Hz, 1H), 7.71 (d, J=2.02 Hz, 1H), 7.53-7.60 (m, 1H), 3.68 (dd, J=10.86, 7.83 Hz, 2H), 3.36 (dd, J=10.86, 3.28 Hz, 2H), 3.03-3.11 (m, 2H), 2.97-3.03 (m, 2H), 2.75 (dd, J=11.12, 3.03 Hz, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-8cf16b07741040668be7c177147891dd
Source dataset
uspto-grants-2015_05
Patent number
US09040712B2

Reaction notes

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