1-(5-fluoro-benzo[b]thiophen-3-ylmethyl)-3-[(methoxycarbonyl-methyl-amino)-methyl]-1H-indole-2-carboxylic acid ethyl ester → HCID 23582108, compound

HRID 642721Notes

Reaction equation

HRID 642721 reaction equation
C(OC(C1N(CC2C3C=C(F)C=CC=3SC=2)C2C(C=1C=O)=CC=CC=2)=O)C.C(OC(C1N(CC2C3C=C(F)C=CC=3SC=2)C2C(C=1CNC)=CC=CC=2)=O)C.C([O:58][C:59]([C:61]1[N:62]([CH2:77][C:78]2[C:79]3[CH:86]=[C:85]([F:87])[CH:84]=[CH:83][C:80]=3[S:81][CH:82]=2)[C:63]2[C:68]([C:69]=1[CH2:70][N:71]([C:73]([O:75][CH3:76])=[O:74])[CH3:72])=[CH:67][CH:66]=[CH:65][CH:64]=2)=[O:60])C>>[F:87][C:85]1[CH:84]=[CH:83][C:80]2[S:81][CH:82]=[C:78]([CH2:77][N:62]3[C:63]4[C:68](=[CH:67][CH:66]=[CH:65][CH:64]=4)[C:69]([CH2:70][N:71]([C:73]([O:75][CH3:76])=[O:74])[CH3:72])=[C:61]3[C:59]([OH:60])=[O:58])[C:79]=2[CH:86]=1

Participants

4

Reactant 3

HCID 685780461-(5-fluoro-benzo[b]thiophen-3-ylmethyl)-3-[(methoxycarbonyl-methyl-amino)-methyl]-1H-indole-2-carboxylic acid ethyl esterHCID 685792281-(5-fluoro-benzo[b]thiophen-3-ylmethyl)-3-methylaminomethyl-1H-indole-2-carboxylic acid ethyl ester2×HCID 866131951-(5-fluoro-benzo[b]thiophen-3-ylmethyl)-3-formyl-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 23582108HCID 23582108, compound

Procedure

1-(5-Fluoro-benzo[b]thiophen-3-ylmethyl)-3-formyl-1H-indole-2-carboxylic acid ethyl ester (from Example 115.1.) was converted to 1-(5-fluoro-benzo[b]thiophen-3-ylmethyl)-3-methylaminomethyl-1H-indole-2-carboxylic acid ethyl ester as described in Example 86.1. 117.2. 1-(5-fluoro-benzo[b]thiophen-3-ylmethyl)-3-methylaminomethyl-1H-indole-2-carboxylic acid ethyl ester was converted to 1-(5-fluoro-benzo[b]thiophen-3-ylmethyl)-3-[(methoxycarbonyl-methyl-amino)-methyl]-1H-indole-2-carboxylic acid ethyl ester as described in Example 77.1. which was hydrolyzed as described in the general procedure B (Exp. 2.2) to give 1-(5-fluoro-benzo[b]thiophen-3-ylmethyl)-3-[(methoxycarbonyl-methyl-amino)-methyl]-1H-indole-2-carboxylic acid as a white solid. MS: 425.5 ([M−H]−).

Sources & evidence

ORD record
ord-809fa9af975a4205abce3bd91be69903
Source dataset
uspto-grants-2010_04
Patent number
US07696240B2

Reaction notes

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