Pyrrolidine → HCID 57732688, compound

HRID 1806392Notes

Reaction equation

HRID 1806392 reaction equation
[C:1]([C:4]1[S:8][CH:7]=[C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[C:16]([C:18]([NH2:20])=[O:19])[CH:17]=2)[NH:14][CH:13]=[C:12]3[CH:21]2[CH2:26][CH2:25][N:24]([S:27]([CH2:30][CH3:31])(=[O:29])=[O:28])[CH2:23][CH2:22]2)[CH:5]=1)(=O)[CH3:2].C([BH3-])#N.[Na+].[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>>[CH2:30]([S:27]([N:24]1[CH2:23][CH2:22][CH:21]([C:12]2[C:11]3[C:15](=[C:16]([C:18]([NH2:20])=[O:19])[CH:17]=[C:9]([C:6]4[CH:5]=[C:4]([C@H:1]([N:36]5[CH2:40][CH2:39][CH2:38][CH2:37]5)[CH3:2])[S:8][CH:7]=4)[CH:10]=3)[NH:14][CH:13]=2)[CH2:26][CH2:25]1)(=[O:29])=[O:28])[CH3:31]

Participants

4

Reactant 3

HCID 31268PyrrolidineHCID 5003444Sodium cyanoborohydrideHCID 66723400HCID 66723400, compound

Product 1

HCID 57732688HCID 57732688, compound

Procedure

To 5-(5-acetyl-3-thienyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (10 mg, 0.02 mmol) was added sodium cyanoborohydride (7.5 mg, 0.12 mmol) and pyrrolidine (0.03 mL, 0.30 mmol). The resulting mixture was reacted in a microwave for 40 min at 150° C. All the solvent was evaporated and the crude product was partitioned between ethyl acetate (1.5 mL) and 1 M sodium hydroxide (0.2 mL). The reaction was purified by SFC to give the title compound as 100% chirally pure.

Workup

  1. customThe resulting mixture was reacted in a microwave for 40 min at 150° C
  2. customAll the solvent was evaporated
  3. customthe crude product was partitioned between ethyl acetate (1.5 mL) and 1 M sodium hydroxide (0.2 mL)
  4. customThe reaction was purified by SFC

Sources & evidence

ORD record
ord-7c9f8e0b1063425a8fdfc6cd6a36661a
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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