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

HRID 1615781Notes

Reaction equation

HRID 1615781 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][C:19]=1[NH:20][C:21](=[O:51])[CH2:22][N:23]1[C:28](=[O:29])[C:27]3([CH2:35][O:34][CH2:33][CH2:32][O:31][CH2:30]3)[N:26](C(OC(C)(C)C)=O)[CH2:25][C@H:24]1[C:43]1[CH:48]=[C:47]([F:49])[CH:46]=[C:45]([F:50])[CH:44]=1)[CH2:16][C:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:15])[CH2:5]2.Cl>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][C:19]=1[NH:20][C:21](=[O:51])[CH2:22][N:23]1[C:28](=[O:29])[C:27]3([CH2:35][O:34][CH2:33][CH2:32][O:31][CH2:30]3)[NH:26][CH2:25][C@H:24]1[C:43]1[CH:44]=[C:45]([F:50])[CH:46]=[C:47]([F:49])[CH:48]=1)[CH2:16][C:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:15])[CH2:5]2

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 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

Product 1

HCID 49842605N-(5-chloro-2'-oxo-1,1',2',3-tetrahydrospiro[inden-2,3'-pyrrolo[2,3-b]pyridin]-6-yl)-2-((R)-3-(3,5-difluorophenyl)-5-oxo-8,11-dioxa-1,4-diazaspiro[5.6]dodecan-4-yl)acetamide

Conditions

Temperature
50 °C

Procedure

40 mg (0.06 mmol) (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 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. The residue was taken up in water and adjusted to pH=8 with saturated NaHCO3 solution. The precipitate formed was suction filtered, washed with water and dried.

Workup

  1. concentrationThe reaction mixture was concentrated by rotary evaporation
  2. customThe precipitate formed
  3. filtrationfiltered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c77505e0855d44599df9cc27cdf5fb27
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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