Cyclopropylamine → {5-[(Cyclopropylamino)methyl]-2-thienyl}boronic acid
Reaction equation
C(NCC1SC(C2C=C3C(=C(C(N)=O)C=2)NC=C3[CH:22]2[CH2:27][CH2:26][N:25](S(CC)(=O)=O)CC2)=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(N)CC1.[BH3-]C#N.[Na+]>>[CH:26]1([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]1Participants
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), cyclopropylamine (0.022 mL, 0.32 mmol), and NaCNBH3 (40 mg, 0.64 mmol) were reacted to give 63 mg of crude {5-[(cyclopropylamino)methyl]-2-thienyl}boronic acid. The crude {5-[(cyclopropylamino)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 impure title compound. The impure title compound was purified again with the Agilent MDAP and isolated as the free base according to the procedure shown in Example 5 to give 6.8 mg of the title compound (7.2%).
Workup
- customwere reacted
Sources & evidence
- ORD record
- ord-058f24104fa744809e8103214d9f3893
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354406B2
Reaction notes
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