Butylamine → HCID 66722834, compound

HRID 1806357Notes

Reaction equation

HRID 1806357 reaction equation
C(S(N1CCC(C2C3C(=C(C(N)=O)C=C([C:21]4[S:22][C:23]([CH2:26][NH:27][CH2:28][CH:29](C)[CH2:30][CH3:31])=[CH:24][CH:25]=4)C=3)NC=2)CC1)(=O)=O)C.C(C1SC([B:43]([OH:45])[OH:44])=CC=1)=O.C(N)CCC.[BH3-]C#N.[Na+]>>[CH2:28]([NH:27][CH2:26][C:23]1[S:22][C:21]([B:43]([OH:45])[OH:44])=[CH:25][CH:24]=1)[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 4

HCID 8007ButylamineHCID 27734305-Formyl-2-thiopheneboronic acidHCID 5003444Sodium cyanoborohydrideHCID 577327913-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[(2-methylbutyl)amino]methyl}-2-thienyl)-1H-indole-7-carboxamide

Product 1

HCID 66722834HCID 66722834, compound

Procedure

Following the general procedure of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[(2-methylbutyl)amino]methyl}-2-thienyl)-1H-indole-7-carboxamide, (5-formyl-2-thienyl)boronic acid (50 mg, 0.32 mmol), butylamine (24 mg, 0.32 mmol), and NaCNBH3 (40 mg, 0.64 mmol) were reacted to give 49 mg of crude {5-[(butylamino)methyl]-2-thienyl}boronic acid. The crude {5-[(butylamino)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) (4 mg, 0.003 mmol) to give 27.2 mg of the title compound (24%).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-74767251447e4e9a822125c449db04fc
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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