Toluene → HCID 57713868, compound

HRID 1984084Notes

Reaction equation

HRID 1984084 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([Cl:26])[C:5]2[C:10]([C:11]#[C:12][CH2:13][OH:14])=[CH:9][N:8]([CH2:15][C:16]3[C:21]([CH3:22])=[C:20]([O:23][CH3:24])[C:19]([CH3:25])=[CH:18][N:17]=3)[C:6]=2[N:7]=1.Cl.[CH3:28][N:29]([CH2:31][C:32](Cl)=[O:33])[CH3:30].C1(C)C=CC=CC=1>N1C=CC=CC=1>[NH2:1][C:2]1[N:3]=[C:4]([Cl:26])[C:5]2[C:10]([C:11]#[C:12][CH2:13][O:14][C:32](=[O:33])[CH2:31][N:29]([CH3:30])[CH3:28])=[CH:9][N:8]([CH2:15][C:16]3[C:21]([CH3:22])=[C:20]([O:23][CH3:24])[C:19]([CH3:25])=[CH:18][N:17]=3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 11950337HCID 11950337, compoundHCID 139949912-(Dimethylamino)acetyl chloride hydrochloride

Product 1

HCID 57713868HCID 57713868, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-[2-amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-prop-2-yn-1-ol (see example 1, 177 mg, 0.48 mmol) in anhydrous pyridine (3 mL) was treated with N,N-dimethylamino-acetyl chloride hydrochloride (113 mg, 0.72 mmol) at rt for 30 min. Addition of toluene (10 mL) caused the formation of a sticky pellet. The toluene solution was discarded, and the pellet was partitioned between water and DCM. The DCM layer was concentrated, and purifed by flash chromatography (EtOAc/DCM/Et3N 33:66:1, gradually adding MeOH (0-2%)) to afford the title compound. tR=4.51 min. 1H NMR (CDCl3) δ 8.23 (s, 1H), 7.14 (s, 1H), 5.31 (s, 2H), 5.00 (s, 2H), 4.98 (s, 2H), 3.76 (s, 3H), 3.25 (s, 2H), 2.38 (s, 6H), 2.28 (s, 3H), 2.20 (s, 3H).

Workup

  1. customthe pellet was partitioned between water and DCM
  2. concentrationThe DCM layer was concentrated

Sources & evidence

ORD record
ord-0df5758c6fb14e6ba336e8e7da97cc5f
Source dataset
uspto-grants-2009_06
Patent number
US07544672B2

Reaction notes

Loading…