Hydrochloric Acid → Elinzanetant

HRID 2245481Notes

Reaction equation

HRID 2245481 reaction equation
[F:1][C:2]([F:54])([F:53])[C:3]1[CH:4]=[C:5]([C:13]([CH3:52])([CH3:51])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:32]3[C@H:41]([CH2:42][O:43][Si](C(C)(C)C)(C)C)[CH2:40][N:39]4[C@H:34]([CH2:35][O:36][CH2:37][CH2:38]4)[CH2:33]3)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl>CO>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([C:13]([CH3:52])([CH3:51])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:32]3[C@H:41]([CH2:42][OH:43])[CH2:40][N:39]4[C@H:34]([CH2:35][O:36][CH2:37][CH2:38]4)[CH2:33]3)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:4]=[C:3]([C:2]([F:1])([F:54])[F:53])[CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58375785HCID 58375785, compound

Product 1

HCID 16063568Elinzanetant

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[3,5-bis(trifluoromethyl)phenyl]-N-[6-[(7S,9aS)-7-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)hexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl]-4-(4-fluoro-2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamide (D24) (390 mg, 0.498 mmol) was dissolved 17 mL of methanol. To this solution was added concentrated HCl (0.9 mL) at 0° C., and stirring was continued at room temperature for 3 h (complete conversion). The reaction mixture was loaded on a SCX cartridge and washed with MeOH. The product was eluted with 0.5 M methanolic ammonia. The product-containing fractions were evaporated, leaving the target compound as a white solid: 310 mg, 0.464 mmol, 93%.

Workup

  1. washwashed with MeOH
  2. washThe product was eluted with 0.5 M methanolic ammonia
  3. customThe product-containing fractions were evaporated

Sources & evidence

ORD record
ord-c813b4de17a04c4bb621e0f15993920a
Source dataset
uspto-grants-2010_03
Patent number
US07683056B2

Reaction notes

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