Hydrochloric Acid → HCID 9803847, compound

HRID 1823199Notes

Reaction equation

HRID 1823199 reaction equation
C(OC(=O)[NH:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][NH:20][C:21]([C@H:23]2[N:27]3[C:28](=[O:38])[C:29]([NH:33][CH:34]4[CH2:37][CH2:36][CH2:35]4)=[N:30][C:31]([Cl:32])=[C:26]3[CH2:25][CH2:24]2)=[O:22])=[CH:15][CH:14]=1)=[NH:12])C1C=CC=CC=1.Cl.[H][H]>CO.O1CCOCC1.[Pd]>[ClH:32].[C:11]([C:13]1[CH:14]=[CH:15][C:16]([CH2:19][NH:20][C:21]([C@H:23]2[N:27]3[C:28](=[O:38])[C:29]([NH:33][CH:34]4[CH2:37][CH2:36][CH2:35]4)=[N:30][C:31]([Cl:32])=[C:26]3[CH2:25][CH2:24]2)=[O:22])=[CH:17][CH:18]=1)(=[NH:10])[NH2:12]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 140484919HCID 140484919, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9803847HCID 9803847, compoundYield 165.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 23938PalladiumSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the compound obtained from Step H (50 mg) in methanol (2.0 mL) was added HCl in dioxane (4.0 M, 0.13 mL) and 10% Pd/C (20 mg). This mixture was hydrogenated with a hydrogen ballon for 1.0 h. Removal of Pd/C and solvent gave the desired product as a white solid (34 mg, 82%). 1HNMR (300 MHz, DMSO-d6) δ 9.34 (br, 2H), 9.05 (m, 3H), 7.78 (d, J=8.5 Hz, 2H), 7.49 (d, J=8.4 Hz, 2H), 5.02 (m 1H), 4.43–4.31 (m, 3H), 3.5 (s, br), 2.90 (m, 2H), 2.21–2.05 (m, 6H), 1.65 (m, 2H). MS m/e 415(M+1).

Workup

  1. customRemoval of Pd/C and solvent

Sources & evidence

ORD record
ord-d30408d0b7b041649eb501f257937509
Source dataset
uspto-grants-2006_05
Patent number
US07037911B2

Reaction notes

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