Sodium borohydride → HCID 54519295, compound

HRID 1432955Notes

Reaction equation

HRID 1432955 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]1[C:18]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[CH:12]=[C:11]1[CH2:19][N:20]1[C:25](=[O:26])[CH2:24][N:23]([S:27]([CH:30]=[CH:31][C:32]2[S:33][C:34]([Cl:37])=[CH:35][CH:36]=2)(=[O:29])=[O:28])[CH2:22][CH:21]1[C:38](OC)=[O:39])=[O:9])([CH3:6])([CH3:5])[CH3:4].C(OC(N1C2C=CN=CC=2C=C1CN1C(=O)CNCC1C(OC)=O)=O)(C)(C)C.ClC1SC(C=CS(Cl)(=O)=O)=CC=1>CO>[C:3]([O:7][C:8]([N:10]1[C:18]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[CH:12]=[C:11]1[CH2:19][N:20]1[C:25](=[O:26])[CH2:24][N:23]([S:27]([CH:30]=[CH:31][C:32]2[S:33][C:34]([Cl:37])=[CH:35][CH:36]=2)(=[O:29])=[O:28])[CH2:22][CH:21]1[CH2:38][OH:39])=[O:9])([CH3:5])([CH3:6])[CH3:4]

Participants

6

Reactant 4

HCID 4311764Sodium borohydrideHCID 54182443HCID 54182443, compoundHCID 544630642-(5-Chlorothiophen-2-yl)ethenesulfonyl chlorideHCID 69028555HCID 69028555, compound

Product 1

HCID 54519295HCID 54519295, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.005 g, 0.13 mmol) is added to a solution of 2-{4-[2-(5-chloro-thiophen-2-yl)-ethenesulfonyl]-2-(±)-methoxycarbonyl-6-oxo-piperazin-1-ylmethyl}-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (0.04 g, 0.07 mmol), (prepared from 2-(2-(±)-methoxycarbonyl-6-oxo-piperazin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester, EXAMPLE 71, and 2-(5-chloro-thiophen-2-yl)-ethenesulfonyl chloride, EXAMPLE 3, using the procedure described in EXAMPLE 214, Part A) in MeOH (3 mL) at RT. The reaction mixture is stirred for 6 h then quenched with water and concentrated in vacuo. The crude product (0.04 g) is taken onto the next step without further purification.

Workup

  1. customat RT
  2. customthen quenched with water
  3. concentrationconcentrated in vacuo
  4. customThe crude product (0.04 g) is taken onto the next step without further purification

Sources & evidence

ORD record
ord-bee0f9d895c041f8850757b9cd95aef4
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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