Cyclopropylamine → HCID 72706526, compound

HRID 929924Notes

Reaction equation

HRID 929924 reaction equation
[F:1][C:2]1[C:3]([NH:20][CH2:21][C:22]2[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][C:23]=2[F:30])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH2:14][C:15]([O:17]CC)=O)[CH:13]=2)=[N:6][CH:7]=1.[CH:31]1([NH2:34])[CH2:33][CH2:32]1>Cl>[CH:31]1([NH:34][C:15](=[O:17])[CH2:14][N:12]2[CH:13]=[C:9]([NH:8][C:5]3[N:4]=[C:3]([NH:20][CH2:21][C:22]4[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][C:23]=4[F:30])[C:2]([F:1])=[CH:7][N:6]=3)[CH:10]=[N:11]2)[CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 118130490HCID 118130490, compound

Product 1

HCID 72706526HCID 72706526, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Conditions

Temperature
140 °C

Procedure

Ethyl 2-(4-((5-fluoro-4-((2,4,6-trifluorobenzyl)amino)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)acetate I-54 (97 mg, 0.23 mmol, prepared by Procedure B), cyclopropylamine (0.5 mL, 7.2 mmol) and conc. hydrochloric acid (2 drops) were mixed in a vessel and then heated in a microwave reactor at 140° C. for 30 min. The resulting precipitate was collected, triturated in ethyl acetate, filtered, washed with ether and methanol to afford N-cyclopropyl-2-(4-((5-fluoro-4-((2,4,6-trifluorobenzyl)amino)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)acetamide I-4 (24 mg, 0.05 mmol) as a white solid. LC-MS (Method B), RT=5.88 min. (ES+) 436.

Workup

  1. additionwere mixed in a vessel
  2. customThe resulting precipitate was collected
  3. customtriturated in ethyl acetate
  4. filtrationfiltered
  5. washwashed with ether and methanol

Sources & evidence

ORD record
ord-03aa403c10ed4092b68c863b3780a618
Source dataset
uspto-grants-2016_03
Patent number
US09296725B2

Reaction notes

Loading…