Sodium Bicarbonate → (3R)-tert-butyl 3-(3,5-difluorophenyl)-5-oxo-4-(2-oxo-2-(2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridin-6,3'-pyrrolo[2,3-b]pyridin]-3-ylamino)ethyl)-8,11-dioxa-1,4-diaza-spiro[5.6]dodecane-1-carboxylate

HRID 1615758Notes

Reaction equation

HRID 1615758 reaction equation
[C:1]([CH2:4][N:5]1[C:10](=[O:11])[C:9]2([CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12]2)[N:8]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:7][C@H:6]1[C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=1)([OH:3])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:57][C:58]1[CH:59]=[C:60]2[CH2:75][C:65]3([C:73]4[C:68](=[N:69][CH:70]=[CH:71][CH:72]=4)[NH:67][C:66]3=[O:74])[CH2:64][C:61]2=[N:62][CH:63]=1.C(=O)([O-])O.[Na+]>CN(C=O)C>[F:32][C:27]1[CH:26]=[C:25]([C@H:6]2[N:5]([CH2:4][C:1](=[O:3])[NH:57][C:58]3[CH:59]=[C:60]4[CH2:75][C:65]5([C:73]6[C:68](=[N:69][CH:70]=[CH:71][CH:72]=6)[NH:67][C:66]5=[O:74])[CH2:64][C:61]4=[N:62][CH:63]=3)[C:10](=[O:11])[C:9]3([CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17]3)[N:8]([C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[CH2:7]2)[CH:30]=[C:29]([F:31])[CH:28]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57974090HCID 57974090, compoundHCID 68154191tert-butyl (R)-4-carboxymethyl-3-(3,5-difluoro-phenyl)-5-oxo-8,11-dioxa-1,4-diaza-spiro[5.6]dodecane-1-carboxylate

Product 1

HCID 68154406(3R)-tert-butyl 3-(3,5-difluorophenyl)-5-oxo-4-(2-oxo-2-(2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridin-6,3'-pyrrolo[2,3-b]pyridin]-3-ylamino)ethyl)-8,11-dioxa-1,4-diaza-spiro[5.6]dodecane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.13 g (0.28 mmol) tert-butyl (R)-4-carboxymethyl-3-(3,5-difluoro-phenyl)-5-oxo-8,11-dioxa-1,4-diaza-spiro[5.6]dodecane-1-carboxylate in 2 ml DMF were combined with 0.11 g (0.29 mmol) HATU and 0.08 ml (0.60 mmol) TEA and stirred for 3 min at RT. Then 72 mg (0.28 mmol) 3-amino-5,7-dihydrospiro[cyclopenta-[b]pyridin-6.3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one were added and the mixture was stirred overnight at RT. The reaction mixture was poured onto saturated sodium hydrogen carbonate solution. The precipitate formed was suction filtered, washed with water and dried.

Workup

  1. stirringthe mixture was stirred overnight at RT
  2. customThe precipitate formed
  3. filtrationfiltered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-6fbd4eac41c04364a55d76724c56b438
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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