Methylamine → HCID 59248980, compound

HRID 552275Notes

Reaction equation

HRID 552275 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:14][CH2:15][C:16]([C:18]2[S:19][C:20]([CH3:29])=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:22]=2)=[O:17])[CH:5]=[C:6]([CH3:13])[C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][O:11]1.[CH3:30][NH2:31]>CO>[OH:11][CH:10]([CH2:12][NH:31][CH3:30])[CH2:9][O:8][C:7]1[C:6]([CH3:13])=[CH:5][C:4]([CH2:14][CH2:15][C:16]([C:18]2[S:19][C:20]([CH3:29])=[C:21]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:22]=2)=[O:17])=[CH:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86640169HCID 86640169, compound

Product 1

HCID 59248980HCID 59248980, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(3,5-dimethyl-4-oxiranylmethoxy-phenyl)-1-(5-methyl-4-phenyl-thiophen-2-yl)-propan-1-one (33 mg, 82 μmol) and methylamine (0.082 mL, 2 M solution in THF) in methanol (1 mL) is stirred at 65° C. for 4 h and at rt for 18 h. The solvent is removed in vacuo and the residue is purified by prep. HPLC to give 3-[4-(2-hydroxy-3-methylamino-propoxy)-3,5-dimethyl-phenyl]-1-(5-methyl-4-phenyl-thiophen-2-yl)-propan-1-one (4 mg) as a colourless resin; LC-MS: tR=0.88 min, [M+1]+=438.25, 1H NMR (as formate salt) (CDCl3): δ 8.56 (s, 1H), 7.60 (s, 1H), 7.45-7.30 (m, 5H), 6.85 (m, 2H), 4.60 (s br, 2H), 4.37-4.30 (m, 1H), 3.81-3.20 (m, 2H), 3.18-3.10 (m, 4H), 2.96-2.88 (m, 2H), 2.70 (s, 3H), 2.51 (s, 3H), 2.20 (s, 6H).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by prep

Sources & evidence

ORD record
ord-4b509d00d1db4511ac4a24eb23e9e4e1
Source dataset
uspto-grants-2011_05
Patent number
US07951794B2

Reaction notes

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