Dimethylformamide → HCID 86705480, compound

HRID 2279464Notes

Reaction equation

HRID 2279464 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:23])[CH2:9][C@H:10]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([F:22])[CH:16]=1)[CH2:11][C:12]([OH:14])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=[N:39][C:34]2[CH:35]=[CH:36][CH:37]=[N:38][C:33]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[CH2:49][N:50](C(C)C)[CH:51]([CH3:53])[CH3:52].[CH3:57][N:58](C=O)C>CCOC(C)=O>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C@H:10]([CH2:11][C:12]([N:38]2[CH2:37][CH2:36][C:35]3[CH:57]=[N:58][C:49]([NH:50][CH:51]([CH3:53])[CH3:52])=[N:39][C:34]=3[CH2:33]2)=[O:14])[CH2:9][N:8]([CH3:23])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:16][C:17]=1[F:22]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68294084HCID 68294084, compound

Product 1

HCID 86705480HCID 86705480, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 72 (102 mg, 0.401 mmol) and 104 (126 mg, 0.364 mmol) and HATU (152 mg, 0.401 mmol) in DMF (5 mL) was added DIPEA (190 μL, 1.09 mmol). The reaction mixture was stirred at RT for 18 h. The reaction was diluted with EtOAc and washed with 1M HCl, satd. aq. NaHCO3, dried (Na2SO4), filtered and concentrated. The crude product was purified by reverse phase column chromatography (SP4) eluting with a MeCN/H2O gradient (5 to 95% MeCN) to afford 102 mg (53.8%) of (S)-tert-butyl 2-(4-chloro-3-fluorophenyl)-4-(2-(isopropylamino)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)-4-oxobutyl(methyl)carbamate (106).

Workup

  1. washwashed with 1M HCl
  2. dry with materialaq. NaHCO3, dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by reverse phase column chromatography (SP4)
  6. washeluting with a MeCN/H2O gradient (5 to 95% MeCN)

Sources & evidence

ORD record
ord-ebc29fbcf738426e92a622435dfe609f
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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