HCID 140484913, compound → HCID 58630487, compound

HRID 1823205Notes

Reaction equation

HRID 1823205 reaction equation
C(OC(=O)[NH:10][C@@:11]1([CH3:57])[C:15]2=[C:16]([Cl:33])[N:17]=[C:18]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[C:19](=[O:20])[N:14]2[C@H:13]([C:34](=[O:56])[NH:35][CH2:36][C:37]2[CH:42]=[CH:41][C:40]([C:43]([NH:45]C(OCC3C=CC=CC=3)=O)=[NH:44])=[CH:39][CH:38]=2)[CH2:12]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:43]([C:40]1[CH:39]=[CH:38][C:37]([CH2:36][NH:35][C:34]([C@H:13]2[N:14]3[C:19](=[O:20])[C:18]([NH:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[CH:24]=4)=[N:17][C:16]([Cl:33])=[C:15]3[C@@:11]([NH2:10])([CH3:57])[CH2:12]2)=[O:56])=[CH:42][CH:41]=1)(=[NH:44])[NH2:45]

Participants

5

Reactant 2

HCID 140484913HCID 140484913, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58630487HCID 58630487, compoundYield 112.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The compound (34 mg, 0.0325 mmol) obtained from Step B was dissolved in MeOH (0.5 mL) and 10% Pd/C (7 mg) was added. A hydrogen balloon was attached and the reaction allowed to stir for approximately 4 h at which time MS indicated a complete reaction. The reaction was filtered and concentrated under vacuum to give the product as a white solid (20 mg, 79% yield). 1HNMR (300 MHz, CD3OD) δ 1.56 (s, 3H) 2.25 (m, 1H) 2.45 (m, 1H) 4.5 (m, 2H) 4.6 (m, 2H) 5.1 (m, 1H) 7.5–7.8 (m, 8H).

Workup

  1. customa complete reaction
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-35082ef7328a49d0a6a365336118479d
Source dataset
uspto-grants-2006_05
Patent number
US07037911B2

Reaction notes

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