Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → (R)-tert-butyl 5-oxo-4-(2-oxo-2-((R)-2'-oxo-1,1',2',3-tetrahydrospiro[inden-2,3'-pyrrolo-[2,3-b]pyridin]-5-ylamino)ethyl)-3-phenyl-8,11-dioxa-1,4-diazaspiro[5.6]-dodecane-1-carboxylate

HRID 1615782Notes

Reaction equation

HRID 1615782 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:13]2([CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14]2)[C:12](=[O:20])[N:11]([CH2:21][C:22]([OH:24])=O)[C@H:10]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:55][C:56]1[CH:57]=[C:58]2[C:71](=[CH:72][CH:73]=1)[CH2:70][C@@:60]1([C:68]3[C:63](=[N:64][CH:65]=[CH:66][CH:67]=3)[NH:62][C:61]1=[O:69])[CH2:59]2>CN(C=O)C>[O:20]=[C:12]1[C:13]2([CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14]2)[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:9][C@@H:10]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:11]1[CH2:21][C:22](=[O:24])[NH:55][C:56]1[CH:57]=[C:58]2[C:71](=[CH:72][CH:73]=1)[CH2:70][C@:60]1([C:68]3[C:63](=[N:64][CH:65]=[CH:66][CH:67]=3)[NH:62][C:61]1=[O:69])[CH2:59]2

Participants

5

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 54776259(S)-5-amino-1,3-dihydrospiro[indene-2,3-pyrrolo[2,3-b]pyridin]-2(1H)-oneHCID 68154418(R)-2-(1-(tert-butoxycarbonyl)-5-oxo-3-phenyl-8,11-dioxa-1,4-diazaspiro[5.6]dodecan-4-yl)ethanoic acid

Product 1

HCID 49842606(R)-tert-butyl 5-oxo-4-(2-oxo-2-((R)-2'-oxo-1,1',2',3-tetrahydrospiro[inden-2,3'-pyrrolo-[2,3-b]pyridin]-5-ylamino)ethyl)-3-phenyl-8,11-dioxa-1,4-diazaspiro[5.6]-dodecane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.21 g (0.5 mmol) (R)-2-(1-(tert-butoxycarbonyl)-5-oxo-3-phenyl-8,11-dioxa-1,4-diaza-spiro[5.6]dodecan-4-yl)ethanoic acid in 3 ml DMF were combined with 0.38 g (1 mmol) HATU and 0.18 ml (1.3 mmol) TEA and stirred for 10 min at RT. Then 0.13 mg (0.5 mmol) (S)-5-amino-1,3-dihydrospiro[inden-2,3′-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 ice water. The precipitate formed was suction filtered, washed with water and dried.

Workup

  1. stirringthe mixture was stirred overnight at RT
  2. additionThe reaction mixture was poured onto ice water
  3. customThe precipitate formed
  4. filtrationfiltered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-c75b51f505d442dda74397577c5f8095
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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