HCID 66893273, compound → HCID 66892876, compound

HRID 532824Notes

Reaction equation

HRID 532824 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[C:4]=1[N:12]1[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]2[S:24][C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:22][CH:21]=2)[CH2:14][CH2:13]1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[C:4]([N:12]2[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[S:24][C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:22][CH:21]=3)[CH2:14][CH2:13]2)=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 66893273HCID 66893273, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66892876HCID 66892876, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(2-methoxy-6-nitrophenyl)-4-(2-phenylthiazol-5-ylmethyl)-[1,4]diazepane (250 mg), 5% Pd/C (20 mg) in 50 mL of ethyl acetate was subjected to a Parr shaker at 65 psi of hydrogen for 16 hours. More 5% Pd/C (10 mg) was added and the reaction continued for another 16 hours. Filtration through celite followed by flash chromatography (0 to 10% MeOH in ethyl acetate) gave 3-methoxy-2-[4-(2-phenylthiazol-5-ylmethyl)-[1,4]diazepan-1-yl]-phenylamine (210 mg, 90%). MS (ES) m/z 395.1 (M+H+).

Workup

  1. filtrationFiltration through celite

Sources & evidence

ORD record
ord-e713278178e44c55a347c6438c169bc4
Source dataset
uspto-grants-2014_10
Patent number
US08853202B2

Reaction notes

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