Hydrochloric Acid → HCID 25206130, compound

HRID 387640Notes

Reaction equation

HRID 387640 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:43]=[C:44]([F:46])[CH:45]=1)[CH2:5][C@H:6]([NH:24][C:25]([C:27]1[C:28]2[CH2:29][CH2:30][N:31]([CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:32](=[O:37])[C:33]=2[CH:34]=[CH:35][CH:36]=1)=[O:26])[C@H:7]([OH:23])[CH2:8][NH:9][C:10]1([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[CH2:12][CH2:11]1.[ClH:47]>C(OCC)C>[ClH:47].[F:1][C:2]1[CH:3]=[C:4]([CH:43]=[C:44]([F:46])[CH:45]=1)[CH2:5][C@H:6]([NH:24][C:25]([C:27]1[C:28]2[CH2:29][CH2:30][N:31]([CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:32](=[O:37])[C:33]=2[CH:34]=[CH:35][CH:36]=1)=[O:26])[C@H:7]([OH:23])[CH2:8][NH:9][C:10]1([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:20])[F:22])[CH:14]=2)[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 25206131HCID 25206131, compound

Product 1

HCID 25206130HCID 25206130, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

360 mg of N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-1-oxo-2-pentyl-1,2,3,4-tetrahydroisoquinoline-5-carboxamide are stirred under an inert atmosphere in 6 cm3 of ethyl ether at a temperature close to 5° C. 1.9 cm3 of a 2M solution of hydrochloric acid in ether are added. The solution is concentrated under reduced pressure (5 kPa). Ethyl ether is added. The suspension is stirred then, after stopping the stirring, the supernatant is removed. Ethyl ether is again added. This operation is carried out several times. The last suspension is then concentrated under reduced pressure (5 kPa). 363 mg of N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-1-oxo-2-pentyl-1,2,3,4-tetrahydroisoquinoline-5-carboxamide hydrochloride (1:1) are obtained in the form of a white solid.

Workup

  1. customclose to 5° C
  2. concentrationThe solution is concentrated under reduced pressure (5 kPa)
  3. additionEthyl ether is added
  4. customthe supernatant is removed
  5. additionEthyl ether is again added
  6. concentrationThe last suspension is then concentrated under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-fdfb5a0a068a429bbc0af424a5b3f783
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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