3,3,3-Trifluoropropylamine → HCID 71290256, compound

HRID 536521Notes

Reaction equation

HRID 536521 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][C:5]1[N:6]=[C:7]([C:14]2[N:15]=[C:16](I)[C:17]3[C:22]([CH3:24])([CH3:23])[C:21](=[O:25])[NH:20][C:18]=3[N:19]=2)[N:8]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]=12.[F:31][C:32]([F:37])([F:36])[CH2:33][CH2:34][NH2:35]>CN1C(=O)CCC1>[F:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][C:5]1[N:6]=[C:7]([C:14]2[N:15]=[C:16]([NH:35][CH2:34][CH2:33][C:32]([F:37])([F:36])[F:31])[C:17]3[C:22]([CH3:24])([CH3:23])[C:21](=[O:25])[NH:20][C:18]=3[N:19]=2)[N:8]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]=12

Participants

4

Reactant 2

HCID 100013,3,3-TrifluoropropylamineHCID 86705365HCID 86705365, compound

Product 1

HCID 71290256HCID 71290256, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

Under an argon atmosphere, 200 mg (purity 69%, 0.27 mmol) of 2-[8-(2-fluorobenzyl) imidazo[1,5-a]pyrimidin-6-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one (example 52A) was suspended in 3.2 ml of absolute NMP and 607 mg (5.37 mmol) of 3,3,3-trifluoropropan-1-amine was added. The mixture was stirred for 1.5 h at 150° C. in the microwave. The reaction solution was filtered and purified by preparative HPLC (eluent: acetonitrile/water with 0.1% hydrochloric acid, gradient 20:80→100:0). 41 mg (31% of theor.) of the target compound was obtained.

Workup

  1. filtrationThe reaction solution was filtered
  2. custompurified by preparative HPLC (eluent: acetonitrile/water with 0.1% hydrochloric acid, gradient 20:80→100:0)
  3. custom41 mg (31% of theor.) of the target compound was obtained

Sources & evidence

ORD record
ord-8bea4412da804b26b7c49a27a75faaa9
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

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