Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → (3R)-tert-butyl 4-(2-(5-chloro-2'-oxo-1,1',2',3-tetrahydrospiro[inden-2,3'-pyrrolo[2,3-b]pyridin]-6-ylamino)-2-oxoethyl)-3-(3,5-difluorophenyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecane-1-carboxylate

HRID 1615748Notes

Reaction equation

HRID 1615748 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]=[C:29]([F:31])[CH:28]=[C:27]([F: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][C:75]=1[Cl:76])[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>[Cl:76][C:75]1[CH:74]=[C:73]2[C:60](=[CH:59][C:58]=1[NH:57][C:22](=[O:24])[CH2:21][N:11]1[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]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][C@H:10]1[C:25]1[CH:26]=[C:27]([F:32])[CH:28]=[C:29]([F:31])[CH:30]=1)[CH2:61][C:62]1([C:70]3[C:65](=[N:66][CH:67]=[CH:68][CH:69]=3)[NH:64][C:63]1=[O:71])[CH2:72]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 68154191tert-butyl (R)-4-carboxymethyl-3-(3,5-difluoro-phenyl)-5-oxo-8,11-dioxa-1,4-diaza-spiro[5.6]dodecane-1-carboxylateHCID 687617765-amino-6-chloro-1,3-dihydrospiro[inden-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Product 1

HCID 68154278(3R)-tert-butyl 4-(2-(5-chloro-2'-oxo-1,1',2',3-tetrahydrospiro[inden-2,3'-pyrrolo[2,3-b]pyridin]-6-ylamino)-2-oxoethyl)-3-(3,5-difluorophenyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.11 g (0.24 mmol) (R)-2-(1-(tert-butoxycarbonyl)-3-(3,5-difluorophenyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecan-4-yl)acetic acid in 4 ml DMF were combined with 0.11 g (0.3 mmol) HATU and 0.07 ml (0.5 mmol) TEA and stirred for 5 min at RT. Then 70 mg (0.24 mmol) 5-amino-6-chloro-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 purified by HPLC.

Workup

  1. stirringthe mixture was stirred overnight at RT
  2. customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record
ord-505644f8b6b6473da6d4cd52a3bcadc2
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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