Sodium triacetoxyborohydride → HCID 58293505, compound

HRID 1968233Notes

Reaction equation

HRID 1968233 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C@H:16]([CH2:25][C:26]#[N:27])[C:17]([NH:19][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:18].[Cl:28][C:29]1[C:30]([CH:51]=O)=[C:31]2[C:37]([C:38]([OH:40])=[O:39])=[CH:36][N:35]([S:41]([C:44]3[CH:50]=[CH:49][C:47]([CH3:48])=[CH:46][CH:45]=3)(=[O:43])=[O:42])[C:32]2=[N:33][CH:34]=1>C(Cl)Cl>[Cl:28][C:29]1[C:30]([CH2:51][NH:15][C@H:16]([CH2:25][C:26]#[N:27])[C:17]([NH:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)=[O:18])=[C:31]2[C:37]([C:38]([OH:40])=[O:39])=[CH:36][N:35]([S:41]([C:44]3[CH:50]=[CH:49][C:47]([CH3:48])=[CH:46][CH:45]=3)(=[O:42])=[O:43])[C:32]2=[N:33][CH:34]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 582934935-chloro-4-formyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acidHCID 67224236HCID 67224236, compound

Product 1

HCID 58293505HCID 58293505, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of sodium triacetoxyborohydride (26.5 mg, 0.125 mmol) and (R)-2-amino-3-cyano-N-cyclopentylpropanamide (22.70 mg, 0.125 mmol) in DCM (1 mL) was stirred at room temperature for 10 min. The reaction mixture was cooled to 0° C. A solution of 5-chloro-4-formyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (30 mg, 0.063 mmol) in DCM (1 mL) was added. The reaction mixture was stirred at 0° C. for 20 min and then concentrated to afford the title compound. [M+H] calc'd for C26H28ClN5O5S, 544; found, 544.2.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C
  2. stirringThe reaction mixture was stirred at 0° C. for 20 min
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5305d42869c5437baf19a06ea010b17a
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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