Hydrochloric Acid → HCID 59752864, compound

HRID 1909661Notes

Reaction equation

HRID 1909661 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]([CH2:21][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>[CH2:21]([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 68998869HCID 68998869, compound

Product 1

HCID 59752864HCID 59752864, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the product from step 1 (340 mg, 0.927 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 title product as a white solid (264 mg, 84%). The solid was dried under vacuum oven at 50° C. for 15 h: MS; m/z 267 (M+H); LCMS (UV) 99%: HPLC 98.8%. 1H NMR (400 MHz, DMSO-d6) δ 1.61-1.66 (m, 1H), 1.84-1.94 (m, 2H), 2.04-2.09 (m, 1H), 3.13-3.18 (m, 2H), 3.30-3.37 (m, 2H), 3.57 (s, 1H), 3.62-3.67 (m, 1H), 3.79 (s, 2H), 6.63 (d, 2H, J=8.4 Hz), 7.0 (d, 2H, J=8.4 Hz), 7.13-7.19 (m, 3H), 7.24-7.28 (m, 2H), 8.9 (s, 1H), 9.4 (s, 1H).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c8103b86a3144181bfd9301e72bcdbe7
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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