Hydrochloric Acid → HCID 59752966, compound

HRID 1909663Notes

Reaction equation

HRID 1909663 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.Cl>O1CCOCC1>[O:21]([C:18]1[CH:19]=[CH:20][C:15]([NH:14][CH2:13][C@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:16][CH:17]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68996670HCID 68996670, compound

Product 1

HCID 59752966HCID 59752966, compoundYield 119.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the product from step 1 (155 mg, 0.42 mmol) was added 4M HCl in dioxane (6 mL) and the resulting mixture was stirred at rt for 3 h. The solvent was removed in vacuo to obtain the product as a solid (135 mg, 94%). The solid was dried under vacuum oven at 50° C. for 15 h: MS; m/z 269 (M+H): LCMS (UV) 99.6%: Elemental analysis: Calc C, 59.83; H, 6.50; N, 8.21. Found C, 59.69; H, 6.55; N, 7.97. 1H NMR (400 MHz, DMSO-d6) δ 1.64-1.70 (m, 1H), 1.88-1.98 (m, 2H), 2.07-2.12 (m, 1H), 3.16-3.20 (m, 2H), 3.30-3.37 (m, 2H), 3.57 (s, 1H), 3.66-374 (m, 1H), 6.76 (d, 2H, J=8.8 Hz), 6.88 (t, 4H, J=18 Hz), 7.03 (t, 1H, J=16 Hz), 7.30-7.34 (m, 2H), 9.0 (s, 1H), 9.4 (s, 1H).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8a8ca35552594cdb97273887743b1faf
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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