Propanolamine ethyl ether → [5-({[3-(Ethyloxy)propyl]amino}methyl)-2-thienyl]boronic acid

HRID 562182Notes

Reaction equation

HRID 562182 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.[CH2:47]([O:49][CH2:50][CH2:51][CH2:52][NH2:53])[CH3:48].[BH3-]C#N.[Na+]>>[CH2:47]([O:49][CH2:50][CH2:51][CH2:52][NH:53][CH2:37][C:39]1[S:43][C:42]([B:44]([OH:46])[OH:45])=[CH:41][CH:40]=1)[CH3:48]

Participants

5

Reactant 4

HCID 22720Propanolamine ethyl etherHCID 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 66723526[5-({[3-(Ethyloxy)propyl]amino}methyl)-2-thienyl]boronic acidYield 38.6%

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-(ethyloxy)propyl]amine (34 mg, 0.32 mmol), and NaCNBH3 (40 mg, 0.64 mmol) were reacted to give 30 mg of crude [5-({[3-(ethyloxy)propyl]amino}methyl)-2-thienyl]boronic acid. The crude [5-({[3-(ethyloxy)propyl]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 8.1 mg of the title compound (10%).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-dacf45b1afc5467fa0434a060c3c93e6
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

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