Hydrochloric Acid → HCID 178485823, compound

HRID 333497

Reaction equation

HRID 333497 reaction equation
[Cl:1]CCl.CO.[CH3:6][O:7][C:8](=[O:64])[NH:9][C@H:10]([C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]1[NH:22][CH:23]=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][C:35]([NH:38][C:39]([C:41]4[CH:42]=[N:43][C:44]([N:47]5[CH2:52][C@H:51]([CH3:53])[N:50]([C:54](=[O:57])[NH:55][CH3:56])[CH2:49][C@H:48]5[CH3:58])=[CH:45][CH:46]=4)=[O:40])=[CH:34][C:33]=3[O:59][C:60]([F:63])([F:62])[F:61])=[CH:28][CH:27]=2)[N:25]=1)=[O:15])[CH:11]([CH3:13])[CH3:12].[ClH:65]>COC1CCCC1>[ClH:1].[ClH:65].[CH3:6][O:7][C:8](=[O:64])[NH:9][C@H:10]([C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]1[NH:22][CH:23]=[C:24]([C:26]2[CH:27]=[CH:28][C:29]([C:32]3[CH:37]=[CH:36][C:35]([NH:38][C:39]([C:41]4[CH:42]=[N:43][C:44]([N:47]5[CH2:52][C@H:51]([CH3:53])[N:50]([C:54](=[O:57])[NH:55][CH3:56])[CH2:49][C@H:48]5[CH3:58])=[CH:45][CH:46]=4)=[O:40])=[CH:34][C:33]=3[O:59][C:60]([F:63])([F:61])[F:62])=[CH:30][CH:31]=2)[N:25]=1)=[O:15])[CH:11]([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6344DichloromethaneHCID 178485822HCID 178485822, compound

Product 1

HCID 178485823HCID 178485823, compound

Reagents, catalysts & solvents 1

HCID 138539Cyclopentyl methyl etherSolvent

Conditions

Temperature
3 °C

Procedure

Dichloromethane (100 mL) and methanol (50 mL) were added to ((S)-1-{(S)-2-[4-(4′-{[6-((2R,5S)-2,5-dimethyl-4-methylcarbamoyl-piperazin-1-yl)-pyridine-3-carbonyl]-amino}-2′-trifluoromethoxy-biphenyl-4-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (10.17 g, 12.40 mmol) and the solution was stirred for 10 min, then cooled to 3° C. and 3 M of HCl in cyclopentyl methyl ether (12.4 mL) was added dropwise keeping the temperature of the reaction mixture less than 10° C. The water bath was removed and the reaction mixture was stirred for 15 min, and concentrated to about 50 mL. Isopropyl acetate was added and the mixture was concentrated to dryness. The resulting material was vacuum dried at RT overnight and vacuum oven dried at RT over the weekend to provide the title compound (12.2 g).

Workup

  1. customthe temperature of the reaction mixture less than 10° C
  2. customThe water bath was removed
  3. stirringthe reaction mixture was stirred for 15 min
  4. concentrationconcentrated to about 50 mL
  5. additionIsopropyl acetate was added
  6. concentrationthe mixture was concentrated to dryness
  7. customdried at RT overnight
  8. customvacuum oven dried at RT over the weekend

Sources & evidence

ORD record
ord-939c810fe3974aa9a487298711c8c219
Source dataset
uspto-grants-2014_11
Patent number
US08883135B2

Linked notes

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