Hydrochloric Acid → HCID 69457244, compound

HRID 1517635Notes

Reaction equation

HRID 1517635 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:29][CH2:30][CH2:31][NH:32]C(OCC1C=CC=CC=1)=O)=[O:28])=[O:16])[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].[ClH:43].[H][H]>CO.[Pd]>[ClH:43].[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:29][CH2:30][CH2:31][NH2:32])=[O:28])=[O:16])[CH2:9][CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 16223478HCID 16223478, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69457244HCID 69457244, compoundYield 107.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the product from Example 28B (0.53 g, 0.93 mmol) and 10% Pd/C (0.053 g, 0.047 mmol) in methanol (50 mL) and conc. HCl (86 μL, 1.02 mmol) was hydrogenated under 60 psi of hydrogen gas at ambient temperature for 1 h. The resulting mixture was filtered and concentrated to obtain title compound (0.47 g, quantitative yield). 1H NMR (DMSO-d6) δ: 1.28 (s, 9H), 1.84 (m, 1H), 2.46 (m, 1H), 2.85 (m, 1H), 2.94 (m, 1H), 4.65 (dd, 2H), 5.18 (q, 1H), 6.96 (d, 1H), 7.26 (s, 2H), 7.31 (s, 1H), 7.51 (t, 1H), 7.69 (d, 1H), 7.91 (d, 1H), 8.02 (br s, 2H), 8.59 (s, 1H), 9.19 (s, 1H). 1H NMR (methanol-d4) δ: 1.32 (s, 9H), 1.91 (m, 1H), 2.59 (m, 1H), 2.90 (m, 1H), 3.00 (m, 1H), 3.45 (dd, 2H), 4.71 (dd, 21H), 5.30 (t, 1H), 7.28 (s, 2H), 7.32 (s, 1H), 7.57 (t, 1H), 7.67 (d, 1H), 7.90 (d, 1H), 8.48 (s, 1H). MS (ESI) m/z: 436.2 [M+H]+ Anal Calcd for C24H29N5O3.HCl.1.8 H2O: C, 57.15; H, 6.71; N, 13.88. Found: C, 57.21; H, 6.55; N, 13.60.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4bc0d88139334b1290de774bb8a5a415
Source dataset
uspto-grants-2012_07
Patent number
US08232309B2

Reaction notes

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