Hydrochloric Acid → HCID 71542077, compound

HRID 1776631Notes

Reaction equation

HRID 1776631 reaction equation
C(OC([N:8]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([O:23][C@H:24]([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH:42]([F:44])[F:43])=[C:37]([O:45][CH2:46][CH:47]3[CH2:49][CH2:48]3)[CH:36]=2)[CH2:25][C:26]2[C:31]([Cl:32])=[CH:30][N+:29]([O-:33])=[CH:28][C:27]=2[Cl:34])=[O:22])=[CH:15][CH:14]=1)[S:9]([CH3:12])(=[O:11])=[O:10])=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[Cl:34][C:27]1[CH:28]=[N+:29]([O-:33])[CH:30]=[C:31]([Cl:32])[C:26]=1[CH2:25][C@@H:24]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH:42]([F:43])[F:44])=[C:37]([O:45][CH2:46][CH:47]2[CH2:48][CH2:49]2)[CH:36]=1)[O:23][C:21](=[O:22])[CH2:20][CH2:19][C:16]1[CH:15]=[CH:14][C:13]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 89455515HCID 89455515, compound

Product 1

HCID 71542077HCID 71542077, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-4-(2-(3-(4-(N-(tert-butoxycarbonyl)methylsulfonamido)-phenyl)propanoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-ethyl)-3,5-dichloropyridine 1-oxide (40 mg, 0.05 mmol) was dissolved in DCM (1.5 ml), then HCl 4M in Dioxane (1 ml, 4 mmol) was added, and the mixture was stirred at RT for 5 hours. The reaction was diluted with DCM and washed with water. The organic phase was dried over Na2SO4 and evaporated under vacuum. The crude product was purified by Preparative reverse-phase HPLC to yield 20 mg of final product (Yield: 62%).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated under vacuum
  4. customThe crude product was purified by Preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-b8ed9182dde54b5b8712b82bf76e1904
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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