Diisopropylethylamine → HCID 86685251, compound

HRID 522896Notes

Reaction equation

HRID 522896 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][CH3:8])=[O:6].C(N(C(C)C)C(C)C)C.[Cl:21][C:22]1[N:27]=[C:26]([Cl:28])[C:25]([C:29]#[N:30])=[CH:24][N:23]=1>COCCOC>[Cl:21][C:22]1[N:27]=[C:26]([NH:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([NH:7][CH3:8])=[O:6])[C:25]([C:29]#[N:30])=[CH:24][N:23]=1.[Cl:28][C:26]1[C:25]([C:29]#[N:30])=[CH:24][N:23]=[C:22]([NH:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([NH:7][CH3:8])=[O:6])[N:27]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 6765263-Amino-N-methylbenzamideHCID 140269072,4-Dichloro-5-cyanopyrimidine

Product 2

HCID 86685250HCID 86685250, compoundHCID 86685251HCID 86685251, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To 3-amino-N-methylbenzamide (353 mg, 2.351 mmol) in DME (8 mL) at 0° C. was added N-ethyl-N-isopropylpropan-2-amine (1.024 mL, 5.88 mmol) followed by 2,4-dichloropyrimidine-5-carbonitrile (450.0 mg, 2.59 mmol). The resulting reaction mixture was allowed to warm to RT (ice melt) over 3 h, concentrated, purified using MPLC (25 g cartridge, 40 g column, 0 to 100% EtOAc-hexanes). Separation of 2- and 4-substitution products was not achieved. Fractions with both products were combined and concentrated giving about a 3:1 mixture of 3-(2-chloro-5-cyanopyrimidin-4-ylamino)-N-methylbenzamide and 3-(4-chloro-5-cyanopyrimidin-2-ylamino)-N-methylbenzamide (172.7 mg).

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated
  3. custompurified
  4. customSeparation of 2- and 4-substitution products
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b621092f9a3d479997dc7c651fce12cb
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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