Dimethylformamide → HCID 178481755, compound

HRID 1628092Notes

Reaction equation

HRID 1628092 reaction equation
[CH3:1][N:2]1[C:6]2=[C:7]3[CH:13]=[C:12]([C:14]4[N:15]([CH2:19][C:20]([OH:22])=O)[CH:16]=[CH:17][CH:18]=4)[NH:11][C:8]3=[N:9][CH:10]=[C:5]2[CH:4]=[N:3]1.C(Cl)(=O)C([Cl:26])=O.CN(C=O)C>C(Cl)Cl>[CH3:1][N:2]1[C:6]2=[C:7]3[CH:13]=[C:12]([C:14]4[N:15]([CH2:19][C:20]([Cl:26])=[O:22])[CH:16]=[CH:17][CH:18]=4)[NH:11][C:8]3=[N:9][CH:10]=[C:5]2[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 178481756HCID 178481756, compound

Product 1

HCID 178481755HCID 178481755, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask was added 2-(2-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-pyrrol-1-yl)acetic acid (0.125 g, 0.423 mmol, Example #AN.1.2) and oxalyl chloride (0.275 mL, 0.550 mmol) in DCM (4 mL) followed by a drop of DMF. The mixture was stirred for about 40 min at rt and then concentrated to dryness to afford 2-(2-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-pyrrol-1-yl)acetyl chloride. The mixture was used immediately in the next step. Analytics were performed by quenching a sample with MeOH and methyl ester is the observed (M+H)+: LC/MS (Table 2, Method c) Rt=1.30 min; MS m/z 310 (M+H)+.

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f99026ccb6f54a57a42e700c85b51908
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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