3,3-Dimethylbutylamine → HCID 66723391, compound

HRID 1806380Notes

Reaction equation

HRID 1806380 reaction equation
C(C(CC)CNCC1SC(C2C=C3C(=C(C(N)=O)C=2)NC=C3C2CCN(S(CC)(=O)=O)CC2)=CC=1)C.[CH:37]([C:39]1[S:43][C:42]([B:44]([OH:46])[OH:45])=[CH:41][CH:40]=1)=O.[CH3:47][C:48]([CH3:53])([CH3:52])[CH2:49][CH2:50][NH2:51].[BH3-]C#N.[Na+]>>[CH3:47][C:48]([CH3:53])([CH3:52])[CH2:49][CH2:50][NH:51][CH2:37][C:39]1[S:43][C:42]([B:44]([OH:46])[OH:45])=[CH:41][CH:40]=1

Participants

5

Reactant 4

HCID 197093,3-DimethylbutylamineHCID 27734305-Formyl-2-thiopheneboronic acidHCID 5003444Sodium cyanoborohydrideHCID 577326215-(5-{[(2-ethylbutyl)amino]methyl}-2-thienyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

Product 1

HCID 66723391HCID 66723391, compoundYield 38.9%

Procedure

Following the general procedure of 5-(5-{[(2-ethylbutyl)amino]methyl}-2-thienyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide, (5-formyl-2-thienyl)boronic acid (50 mg, 0.32 mmol), (3,3-dimethylbutyl)amine (32 mg, 0.32 mmol), and NaCNBH3 (40 mg, 0.64 mmol) were reacted to give 30 mg of crude (5-{[(3,3-dimethylbutyl)amino]methyl}-2-thienyl)boronic acid. The crude (5-{[(3,3-dimethylbutyl)amino]methyl}-2-thienyl)boronic acid was then reacted with 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (65 mg, 0.157 mmol), K2CO3 (130 mg, 0.942 mmol), and tetrakis(triphenylphosphine)palladium(0) (9 mg, 0.0079 mmol) to give 4.5 mg of the title compound (5%).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-2ee66881c4974a689b4c5f691ca7b27f
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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