Dimethylacetamide → HCID 11439630, compound

HRID 2357880Notes

Reaction equation

HRID 2357880 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[N:3]=1.CN(C)[C:20](=[O:22])[CH3:21]>O>[N:15]1[CH:16]=[CH:17][C:12]([C:4]2[N:3]=[C:2]([NH:3][C@H:2]3[C:11]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH2:21][C@H:20]3[OH:22])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 31374DimethylacetamideHCID 47368494-chloro-2-pyridin-4-ylquinazoline

Product 1

HCID 11439630HCID 11439630, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

4-Chloro-2-pyridin-4-ylquinazoline (1 mmol) was dissolved into N,N-dimethylacetamide (0.5 M), followed by addition of diispropylethylamine (2 mmol) and 1S, 2R-(−)-cis-1-amino-2-indanol (1.2 mmol) and was stirred at 85° C. for 2 h. The reaction was poured into water and back-extracted with ethyl acetate (3×). The combined organic layers were washed with 1N HCl, followed by a brine wash, and dried over magnesium sulfate. The final product was purified by MPLC and lyophilized to a yellow powder. (78%) 1H NMR (400 MHz, d6-DMSO): δ 8.75 (d, 2H), 8.55 (d, 1H), 8.35 (m, 2H), 7.85 (d, 2H), 7.55 (m, 1H), 7.35 (d, 2H), 7.25 (m, 2H), 6.15 (m, 1H), 4.85 (m, 1H), 3.25 (dd, 1H), 3.00 (d, 1H). MS (EI) for C22H18N4O: 355 (MH+).

Workup

  1. extractionback-extracted with ethyl acetate (3×)
  2. washThe combined organic layers were washed with 1N HCl
  3. washwash
  4. dry with materialdried over magnesium sulfate
  5. customThe final product was purified by MPLC

Sources & evidence

ORD record
ord-7ce54c7988574aaca639241235c562db
Source dataset
uspto-grants-2010_07
Patent number
US07763627B2

Reaction notes

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