1-Pyrrolidinepropanamine → HCID 67390378, compound

HRID 406119Notes

Reaction equation

HRID 406119 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]3[C:17]([CH3:18])=[C:16]([C:19]([OH:21])=O)[S:15][C:11]=3[N:12]=[CH:13][N:14]=2)=[C:4]([O:22][CH:23]2[CH2:30][CH:26]3[O:27][CH2:28][O:29][CH:25]3[CH2:24]2)[CH:3]=1.[NH2:31][CH2:32][CH2:33][CH2:34][N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[N:35]1([CH2:34][CH2:33][CH2:32][NH:31][C:19]([C:16]2[S:15][C:11]3[N:12]=[CH:13][N:14]=[C:9]([NH:8][C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=4[O:22][CH:23]4[CH2:24][CH:25]5[O:29][CH2:28][O:27][CH:26]5[CH2:30]4)[C:10]=3[C:17]=2[CH3:18])=[O:21])[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 316701-PyrrolidinepropanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67382198HCID 67382198, compound

Product 1

HCID 67390378HCID 67390378, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.15 g 4-[4-fluoro-2-(tetrahydro-cyclopenta[1,3]dioxol-5-yloxy)phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid, 0.045 g 1-(3-aminopropy)pyrrolidine, 0.159 g HATU and 0.097 ml TEA in 15 ml DMF was stirred at rt for 1 hour. The reaction mixture was poured on water, extracted with DCM, dried and filtered. The filtrate was concentrated. The residue was triturated with diisopropylether.

Workup

  1. additionThe reaction mixture was poured on water
  2. extractionextracted with DCM
  3. customdried
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customThe residue was triturated with diisopropylether

Sources & evidence

ORD record
ord-09f9c8f2064543398860491cccdbdfa9
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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