Isoamylamine → HCID 66722973, compound

HRID 1806362Notes

Reaction equation

HRID 1806362 reaction equation
C(S([N:6]1C[CH2:10][CH:9]([C:12]2C3C(=C(C(N)=O)C=C(C4SC(CNCC(C)CC)=CC=4)C=3)NC=2)[CH2:8][CH2:7]1)(=O)=O)C.[CH:36]([C:38]1[S:42][C:41]([B:43]([OH:45])[OH:44])=[CH:40][CH:39]=1)=O.CC(C)CCN.[BH3-]C#N.[Na+]>>[CH3:10][CH:9]([CH3:12])[CH2:8][CH2:7][NH:6][CH2:36][C:38]1[S:42][C:41]([B:43]([OH:45])[OH:44])=[CH:40][CH:39]=1

Participants

5

Reactant 4

HCID 7894IsoamylamineHCID 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 66722973HCID 66722973, 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), (3-methylbutyl)amine (28 mg, 0.32 mmol), and NaCNBH3 (40 mg, 0.64 mmol) were reacted to give 46 mg of crude (5-{[(3-methylbutyl)amino]methyl}-2-thienyl)boronic acid. The crude (5-{[(3-methylbutyl)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) (4 mg, 0.003 mmol) to give 38.3 mg of the title compound (37%).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-8d419bff4c7c421d96aa68f5265dae89
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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