(S)-(+)-Tetrahydrofurfurylamine → 5-[3-({[(1S)-1,2-dimethylpropyl]amino}methyl)-5-fluorophenyl]-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

HRID 562262

Reaction equation

HRID 562262 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([S:10]([N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[C:27]3[C:22](=[C:23]([C:43]([NH2:45])=[O:44])[CH:24]=[C:25]([C:28]4[CH:33]=[C:32]([CH2:34][NH:35][CH2:36][C@@H:37]5CCCO5)[CH:31]=[C:30]([F:42])[CH:29]=4)[CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1)(=[O:12])=[O:11])[CH3:9].O1CC[CH2:48][C@H:47]1[CH2:51]N>>[CH3:37][C@H:36]([NH:35][CH2:34][C:32]1[CH:33]=[C:28]([C:25]2[CH:26]=[C:27]3[C:22](=[C:23]([C:43]([NH2:45])=[O:44])[CH:24]=2)[NH:21][CH:20]=[C:19]3[CH:16]2[CH2:15][CH2:14][N:13]([S:10]([CH2:8][CH3:9])(=[O:11])=[O:12])[CH2:18][CH2:17]2)[CH:29]=[C:30]([F:42])[CH:31]=1)[CH:47]([CH3:51])[CH3:48]

Participants

3

Reactant 2

HCID 641530(S)-(+)-TetrahydrofurfurylamineHCID 667231363-[1-(ethylsulfonyl)-4-piperidinyl]-5-[3-fluoro-5-({[(2S)-tetrahydro-2-furanylmethyl]amino}methyl)phenyl]-1H-indole-7-carboxamide trifluoroacetate

Product 1

HCID 426302445-[3-({[(1S)-1,2-dimethylpropyl]amino}methyl)-5-fluorophenyl]-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamideYield 42%

Procedure

The title compound was prepared according to the general procedure of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-[3-fluoro-5-({[(2S)-tetrahydro-2-furanylmethyl]amino}methyl)phenyl]-1H-indole-7-carboxamide trifluoroacetate, substituting (2S)-3-methyl-2-butanamine (45 mg, 0.525 mmol) for 1-[(2S)-tetrahydro-2-furanyl]methanamine to afford 19.3 mg of the title compound (42%).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-4a4872015e3f4d7ea201b85ce4a2331a
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Linked notes

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