Diisopropylethylamine → HCID 178507159, compound

HRID 32491Notes

Reaction equation

HRID 32491 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:37][C:38]1[N:43]([C:44]2[CH:49]=[CH:48][C:47]([NH2:50])=[CH:46][CH:45]=2)[CH2:42][N:41]=[C:40]2[S:51][CH:52]=[CH:53][C:39]=12.CCN(C(C)C)C(C)C.CO.C(NCC)C>CN(C=O)C>[NH2:37][C:38]1[N:43]([C:44]2[CH:45]=[CH:46][C:47]([NH:50][C:10](=[O:12])[CH2:9][C:3]3[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=3[F:1])=[CH:48][CH:49]=2)[CH2:42][N:41]=[C:40]2[S:51][CH:52]=[CH:53][C:39]=12

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 5228232,5-Difluorophenylacetic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21877050Diethylamine methanolHCID 178507154HCID 178507154, compound

Product 1

HCID 178507159HCID 178507159, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.25 mmoles of the carboxylic acid of choice (2,5-difluorophenyl-acetic acid; 0.25 mmoles) and 0.25 mmoles of HBTU were dissolved in 1 mL amine-free DMF. To this solution was added dropwise a solution of 4-Amino-3-(4-aminophenyl)thieno[2,3-d]-pyrimidine in 1 mL DMF. The resulting solution was treated with 0.3 mL of Hunig's base. The system was stirred at room temperature overnight and then treated with 0.5 mL of 1:1 MeOH-diethylamine. The system was concentrated to dryness in a Speedvac system, reconstituted in 1 mL DMSO and purified by prep HPLC. MH+=397.

Workup

  1. concentrationThe system was concentrated to dryness in a Speedvac system
  2. custompurified by prep HPLC

Sources & evidence

ORD record
ord-20867e3faccc415b9213e14d559f6475
Source dataset
uspto-grants-2008_09
Patent number
US07427623B2

Reaction notes

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