Diisopropylethylamine → HCID 44199820, compound

HRID 2061179Notes

Reaction equation

HRID 2061179 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=O)[CH2:3]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:43][N:44]1[C:53]2[C:48](=[CH:49][N:50]=[C:51]([CH3:54])[CH:52]=2)[CH:47]=[C:46]([C:55]2[CH:56]=[C:57]([NH:62]/[C:63](/[NH2:66])=[N:64]/O)[CH:58]=[CH:59][C:60]=2[CH3:61])[C:45]1=[O:67].[BH4-].[Na+]>CN(C=O)C>[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([C:7]2[O:9][N:64]=[C:63]([NH:62][C:57]3[CH:58]=[CH:59][C:60]([CH3:61])=[C:55]([C:46]4[C:45](=[O:67])[N:44]([CH3:43])[C:53]5[C:48]([CH:47]=4)=[CH:49][N:50]=[C:51]([CH3:54])[CH:52]=5)[CH:56]=3)[N:66]=2)[CH2:3]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 2277983-Oxocyclopentanecarboxylic acidHCID 4311764Sodium borohydrideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178422078HCID 178422078, compound

Product 1

HCID 44199820HCID 44199820, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3-Oxocyclopentanecarboxylic acid (16.6 mg, 0.12 mmol), HATU (50 mg, 0.12 mmol), and DIPEA (0.023 mL, 0.12 mmol) were stirred in dry DMF (3 mL) for 1 h before 17 (40 mg, 0.118 mmol) was added at rt. The stirring was continued for 1 h before it was heated at 100° C. for 5 h. After cooling NaBH4 (20 mg) was added and stirred for 5 h at rt. After filtration, the mixture was purified by preparative LC/MS to give 3-(5-(5-(3-hydroxycyclopentyl)-1,2,4-oxadiazol-3-ylamino)-2-methylphenyl)-1,7-di methyl-1,6-naphthyridin-2(1H)-one (A73) as a solid. MS m/z 431.5, 432.6 (M+1).

Workup

  1. additionwas added at rt
  2. additionwas added
  3. filtrationAfter filtration
  4. customthe mixture was purified by preparative LC/MS

Sources & evidence

ORD record
ord-22c937669cc3412c986af238feec4277
Source dataset
uspto-grants-2012_10
Patent number
US08278452B2

Reaction notes

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