Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → tert-butyl 3-(3-methoxyphenyl)-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)-8,11-dioxa-1,4-diazaspiro[5.6]dodecane-1-carboxylate

HRID 1615746Notes

Reaction equation

HRID 1615746 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](O)=[O:23])[CH:10]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[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.[NH2:57][C:58]1[CH:59]=[C:60]2[C:73](=[CH:74][CH:75]=1)[CH2:72][C@@:62]1([C:70]3[C:65](=[N:66][CH:67]=[CH:68][CH:69]=3)[NH:64][C:63]1=[O:71])[CH2:61]2>CN(C=O)C>[CH3:32][O:31][C:27]1[CH:26]=[C:25]([CH:10]2[N:11]([CH2:21][C:22](=[O:23])[NH:57][C:58]3[CH:59]=[C:60]4[C:73](=[CH:74][CH:75]=3)[CH2:72][C@:62]3([C:70]5[C:65](=[N:66][CH:67]=[CH:68][CH:69]=5)[NH:64][C:63]3=[O:71])[CH2:61]4)[C:12](=[O:20])[C:13]3([CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14]3)[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]2)[CH:30]=[CH:29][CH:28]=1

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 681545282-(1-(Tert-butoxycarbonyl)-3-(3-methoxyphenyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecan-4-yl)ethanoic acid

Product 1

HCID 68154207tert-butyl 3-(3-methoxyphenyl)-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)-8,11-dioxa-1,4-diazaspiro[5.6]dodecane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.44 g (0.81 mmol) 80% 2-(1-(tert-butoxycarbonyl)-3-(3-methoxyphenyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecan-4-yl)ethanoic acid in 10 ml DMF were combined with 0.75 g (2.0 mmol) HATU and 0.34 ml (2.4 mmol) TEA and stirred for 10 min at RT. Then 0.25 g (0.98 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 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 water
  3. customThe precipitate formed
  4. filtrationfiltered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-226a36f335c44a7daeba40ac634ed413
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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