Hydrochloric Acid → HCID 71465413, compound

HRID 1517639Notes

Reaction equation

HRID 1517639 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C@H:10]([NH:14][C:15]([NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=1[CH:20]=[N:21][N:22]3[C:27](=[O:32])[CH2:28][N:29]([CH3:31])[CH3:30])=[O:16])[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].[ClH:33].C(OCC)C>C(OCC)(=O)C.C(OCC)C>[ClH:33].[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C@H:10]([NH:14][C:15]([NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=1[CH:20]=[N:21][N:22]3[C:27](=[O:32])[CH2:28][N:29]([CH3:30])[CH3:31])=[O:16])[CH2:9][CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 16225887HCID 16225887, compound

Product 1

HCID 71465413HCID 71465413, compound

Reagents, catalysts & solvents 1

HCID 21584169Diethylether ethylacetateSolvent

Procedure

The solid from Example 59 was taken up in ethyl acetate/diethyl ether (1/10) (20 mL) and 2N HCl in diethyl ether (2.0 eq) was added dropwise and the mixture was stirred for 5 minutes. The reaction was concentrated in vacuo to give the title compound as a white solid. 1H NMR (DMSO-d6, 300 MHz); δ1.28 (s, 9H), 1.77-1.83 (m, 1H), 2.42-2.53 (m, 1H), 2.73-2.94 (m, 2H), 2.97 (s, 6H), 5.02 (s, 2H), 5.14-5.21 (m, 1H), 7.25-7.35 (m, 4H), 7.58 (t, J=7.80, 15.94 Hz, 1H), 7.83 (d, J=8.14 Hz, 1H), 8.03 (d, J=8.14 Hz, 1H), 8.93(s, 1H), 9.77 (s, 1H). Calc for C25H31N5O2.1.7HCl: C, 60.60; H, 6.65; N, 14.13. Found: C, 60.91; H, 6.87; N, 13.85. MS (DCI/NH3) m/z 434.

Workup

  1. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-afccfaa93ba6454eb6cc68db7acc7ea3
Source dataset
uspto-grants-2012_07
Patent number
US08232309B2

Reaction notes

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