Hydrochloric Acid → HCID 11551917, compound

HRID 1445565Notes

Reaction equation

HRID 1445565 reaction equation
CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.C[O:20][C:21](=[O:33])[CH2:22][C:23]1[C:31]2[C:26](=[N:27][CH:28]=[CH:29][CH:30]=2)[NH:25][C:24]=1[CH3:32].[CH3:34][C:35]1[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1.[OH-].[Na+].Cl>CN(C=O)C>[CH3:32][C:24]1[N:25]([S:41]([C:38]2[CH:39]=[CH:40][C:35]([CH3:34])=[CH:36][CH:37]=2)(=[O:43])=[O:42])[C:26]2=[N:27][CH:28]=[CH:29][CH:30]=[C:31]2[C:23]=1[CH2:22][C:21]([OH:20])=[O:33]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 67218699methyl 2-(2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetate

Product 1

HCID 11551917HCID 11551917, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of BEMP (90 μL, 0.31 mmol) in DMF (400 μL) is added to a solution of (2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester (40 mg, 0.20 mmol) in DMF (400 μL). After 40-50 minutes, a solution of 4-methyl-benzenesulfonyl chloride (60 mg, 0.31 mmol) in DMF (400 μL) is added. After a further 30 minutes, 1M aqueous NaOH (800 μL) is added, and the reaction is shaken mechanically for 105 minutes, then 1M aqueous HCl (800 μL) is added. The reaction is partitioned between water and CH2Cl2. The organic phase is loaded directly onto a pre-packed Isolute™ silica column and eluted with EtOAc to give crude product which is triturated with water to afford [2-methyl-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid; MH+=345.

Workup

  1. waitAfter a further 30 minutes
  2. customThe reaction is partitioned between water and CH2Cl2
  3. washeluted with EtOAc
  4. customto give crude product which
  5. customis triturated with water

Sources & evidence

ORD record
ord-d3c741f0ca3e40a8b866f94df6cdbf35
Source dataset
uspto-grants-2010_02
Patent number
US07666878B2

Reaction notes

Loading…