Cyclopropanemethanamine → (5-{[(Cyclopropylmethyl)amino]methyl}-2-thienyl)boronic acid

HRID 562142Notes

Reaction equation

C(NCC1SC(C2C=C3C(=C(C(N)=O)C=2)NC=C3[CH:22]2[CH2:27]C[N:25](S(CC)(=O)=O)[CH2:24][CH2:23]2)=CC=1)C.[CH:33]([C:35]1[S:39][C:38]([B:40]([OH:42])[OH:41])=[CH:37][CH:36]=1)=O.C1(CN)CC1.[BH3-]C#N.[Na+]>>[CH:23]1([CH2:24][NH:25][CH2:33][C:35]2[S:39][C:38]([B:40]([OH:42])[OH:41])=[CH:37][CH:36]=2)[CH2:22][CH2:27]1

Participants

Reactant 4

HCID 75646Cyclopropanemethanamine

HCID 27734305-Formyl-2-thiopheneboronic acid

HCID 5003444Sodium cyanoborohydride

HCID 577327795-{5-[(ethylamino)methyl]-2-thienyl}-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

Product 1

HCID 66723007(5-{[(Cyclopropylmethyl)amino]methyl}-2-thienyl)boronic acid

Procedure

Following the general procedure of 5-{5-[(ethylamino)methyl]-2-thienyl}-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide, (5-formyl-2-thienyl)boronic acid (50 mg, 0.32 mmol), (cyclopropylmethyl)amine (0.027 mL, 0.32 mmol), and NaCNBH3 (40 mg, 0.64 mmol) were reacted to give 73 mg of crude (5-{[(cyclopropylmethyl)amino]methyl}-2-thienyl)boronic acid. The crude (5-{[(cyclopropylmethyl)amino]methyl}-2-thienyl)boronic acid was then reacted with 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (80 mg, 0.193 mmol), potassium carbonate (160 mg, 1.16 mmol), and tetrakis(triphenylphosphine)palladium(0) (5 mg, 0.004 mmol) to give 19.1 mg of the title compound (20%).

Workup

customwere reacted

Sources & evidence

ORD record: ord-8c616653ec854f1f9573c2e5c8465ced
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063071B2

Reaction notes

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