(S(R*,R*))-2-amino-1-phenylpropane-1,3-diol → 1-[5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-3-((1S,2S)-2-hydroxy-1-hydroxymethyl-2-phenyl-ethyl)-thiourea

HRID 25521Notes

Reaction equation

HRID 25521 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]1[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16]([N:18]=[C:19]=[S:20])[CH:17]=1)=[CH:5]2.[NH2:23][C@@H:24]([CH2:33][OH:34])[C@H:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[OH:26]>>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]1[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16]([NH:18][C:19]([NH:23][C@@H:24]([CH2:33][OH:34])[C@@H:25]([OH:26])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[S:20])[CH:17]=1)=[CH:5]2

Participants

3

Reactant 2

HCID 119881(S(R*,R*))-2-amino-1-phenylpropane-1,3-diolHCID 22568438HCID 22568438, compound2×

Product 1

HCID 102996501-[5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-3-((1S,2S)-2-hydroxy-1-hydroxymethyl-2-phenyl-ethyl)-thiourea

Procedure

The product from Example 35, Step A, 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl isothiocyanate (0.316 g, 1.0 mmol) was reacted with (1S,2S)-(+)-2-amino-1-phenyl-1,3-propanediol (0.167 g, 1.0 mmol) according to the procedure for Example 23, Step B to give the product after trituration with hexanes/ethyl acetate, 1/1, v/v and filtration through silica gel using hexanes/ethyl acetate, 1/1, v/v as eluant The resulting orange oil/foam was triturated with hexanes/ether to give the product as an orange solid (0.155 g), mp (slow decomposition).

Workup

  1. customto give the product after trituration
  2. filtrationwith hexanes/ethyl acetate, 1/1, v/v and filtration through silica gel
  3. customwas triturated with hexanes/ether

Sources & evidence

ORD record
ord-77380d7af45a4e5ebba7356cec34399a
Source dataset
uspto-grants-2005_02
Patent number
US06858739B2

Reaction notes

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