Hydrochloric Acid → 2-((R)-3-(3,5-difluorophenyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecan-4-yl)-N-(2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridin-6,3'-pyrrolo[2,3-b]pyridin]-3-yl)acetamide

HRID 1615785Notes

Reaction equation

HRID 1615785 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[N:14]([CH2:15][C:16](=[O:36])[NH:17][C:18]3[CH:19]=[C:20]4[CH2:35][C:25]5([C:33]6[C:28](=[N:29][CH:30]=[CH:31][CH:32]=6)[NH:27][C:26]5=[O:34])[CH2:24][C:21]4=[N:22][CH:23]=3)[C:13](=[O:37])[C:12]3([CH2:43][O:42][CH2:41][CH2:40][O:39][CH2:38]3)[N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.Cl>>[F:8][C:6]1[CH:5]=[C:4]([C@H:9]2[N:14]([CH2:15][C:16]([NH:17][C:18]3[CH:19]=[C:20]4[CH2:35][C:25]5([C:33]6[C:28](=[N:29][CH:30]=[CH:31][CH:32]=6)[NH:27][C:26]5=[O:34])[CH2:24][C:21]4=[N:22][CH:23]=3)=[O:36])[C:13](=[O:37])[C:12]3([CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43]3)[NH:11][CH2:10]2)[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 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

Product 1

HCID 498427212-((R)-3-(3,5-difluorophenyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecan-4-yl)-N-(2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridin-6,3'-pyrrolo[2,3-b]pyridin]-3-yl)acetamide

Conditions

Temperature
50 °C

Procedure

0.18 g (0.26 mmol) (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-diazaspiro[5.6]dodecane-1-carboxylate were combined with 30 ml of a 1N methanolic hydrochloric acid solution and stirred for 1 h at 50° C. The reaction mixture was concentrated by rotary evaporation and purified by HPLC. The product fractions were evaporated down, neutralised with sodium hydrogen carbonate and the aqueous phase was extracted with DCM. The organic phase was concentrated by rotary evaporation. The residue was triturated with diethyl ether, suction filtered, washed with diethyl ether and dried.

Workup

  1. concentrationThe reaction mixture was concentrated by rotary evaporation
  2. custompurified by HPLC
  3. customThe product fractions were evaporated down
  4. extractionthe aqueous phase was extracted with DCM
  5. concentrationThe organic phase was concentrated by rotary evaporation
  6. customThe residue was triturated with diethyl ether, suction
  7. filtrationfiltered
  8. washwashed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-7acb8a9817404df294b47252eae744f4
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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