2-Pentanamine → HCID 66723475, compound

HRID 562169Notes

Reaction equation

C(S(N1CCC(C2[C:20]3[C:15](=[C:16](C(N)=O)[CH:17]=[C:18](C4SC(CNCC(C)CC)=CC=4)C=3)[NH:14]C=2)CC1)(=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(N)CCC.[BH3-]C#N.[Na+]>>[CH3:20][CH:15]([NH:14][CH2:36][C:38]1[S:42][C:41]([B:43]([OH:45])[OH:44])=[CH:40][CH:39]=1)[CH2:16][CH2:17][CH3:18]

Participants

Reactant 4

HCID 122462-Pentanamine

HCID 27734305-Formyl-2-thiopheneboronic acid

HCID 5003444Sodium cyanoborohydride

HCID 577327913-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[(2-methylbutyl)amino]methyl}-2-thienyl)-1H-indole-7-carboxamide

Product 1

HCID 66723475HCID 66723475, 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), (1-methylbutyl)amine (29 mg, 0.32 mmol), and NaCNBH3 (40 mg, 0.64 mmol) were reacted to give 43 mg of crude (5-{[(1-methylbutyl)amino]methyl}-2-thienyl)boronic acid. The crude (5-{[(1-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 35.2 mg of the title compound (60%).

Workup

customwere reacted

Sources & evidence

ORD record: ord-1143099bc08944308e8599c432b46f2f
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063071B2

Reaction notes

Loading…