Diisopropylethylamine → HCID 71550358, compound

HRID 510200Notes

Reaction equation

HRID 510200 reaction equation
[CH3:1][NH:2][CH3:3].C1COCC1.[CH3:9][CH:10]([CH3:39])[C@@H:11]([NH:20][C:21]1[CH:22]=[C:23]([C:27]2[C:35]3[C:30](=[N:31][CH:32]=[C:33]([C:36](O)=[O:37])[CH:34]=3)[NH:29][CH:28]=2)[CH:24]=[N:25][CH:26]=1)[C:12](=[O:19])[NH:13][CH2:14][C:15]([F:18])([F:17])[F:16].CCN(C(C)C)C(C)C.C(P1(=O)OP(=O)(CCC)OP(=O)(CCC)O1)CC.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:1][N:2]([CH3:3])[C:36]([C:33]1[CH:34]=[C:35]2[C:27]([C:23]3[CH:24]=[N:25][CH:26]=[C:21]([NH:20][C@H:11]([CH:10]([CH3:39])[CH3:9])[C:12](=[O:19])[NH:13][CH2:14][C:15]([F:18])([F:16])[F:17])[CH:22]=3)=[CH:28][NH:29][C:30]2=[N:31][CH:32]=1)=[O:37]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 2724699PyBOPHCID 22320367Dimethylamine tetrahydrofuranHCID 117628654HCID 117628654, compound

Product 1

HCID 71550358HCID 71550358, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a 0° C. solution of 2M dimethylamine/THF (58 uL, 0.115 mmol), 3-(5-(3-methyl-1-oxo-1-(2,2,2-trifluoroethylamino)butan-2-ylamino)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid 3-1b (25 mg, 0.057 mmol) and DIPEA (0.025 ml, 0.144 mmol) in DMF (0.7 ml) was slowly added 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (0.078 ml, 0.115 mmol). The reaction was allowed to warm to room temperature and stir 18 hr. PyBOP (59.8 mg, 0.115 mmol) was then added and let stir 18 hr. The reaction was diluted with DMF (0.7 mL), filtered, and purified by reverse-phase HPLC. Lyophilization of pure fractions gave the title compound as a solid. LRMS (ESI) m/z 463.2 [(M+H)+; calcd for C22H25F3N6O2: 463.2].

Workup

  1. customTo a 0° C.
  2. stirringlet stir 18 hr
  3. filtrationfiltered
  4. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-85aa40b6fefa4a1baf6f51f1b54af584
Source dataset
uspto-grants-2015_08
Patent number
US09096598B2

Reaction notes

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