Hydrochloric Acid → HCID 16063569, compound

HRID 421266Notes

Reaction equation

HRID 421266 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 58375781HCID 58375781, compound

Product 1

HCID 16063569HCID 16063569, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[3,5-bis(trifluoromethyl)phenyl]-N-[6-[(7S,9aR)-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 (D25) (87 mg, 0.111 mmol) was dissolved 4 mL of methanol. To this solution was added concentrated HCl (0.2 mL) at 0° C., and stirred at room temperature for 1 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 UV-active basic fractions were evaporated, leaving the target compound as a white solid: 69 mg, 0.103 mmol, 93%.

Workup

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

Sources & evidence

ORD record
ord-e2c8111e321c49b9a79e7c095015a340
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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