Ammonium Hydroxide → HCID 53251801, compound

HRID 515957Notes

Reaction equation

HRID 515957 reaction equation
Br[CH2:2][C:3]1[C:8]([C:9]([O:11]C)=O)=[C:7]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[N:6]=[C:5]([NH:24][C@@H:25]2[CH2:30][CH2:29][CH2:28][CH2:27][C@@H:26]2[NH:31]C(OC(C)(C)C)=O)[N:4]=1.[OH-].[NH4+:40].[C:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42].C(Cl)Cl>C1COCC1>[C:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42].[NH2:31][C@H:26]1[CH2:27][CH2:28][CH2:29][CH2:30][C@H:25]1[NH:24][C:5]1[N:6]=[C:7]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:22])([F:21])[F:23])[CH:15]=2)[C:8]2[C:9](=[O:11])[NH:40][CH2:2][C:3]=2[N:4]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 21863450Trifluoroacetic acid methylene chlorideHCID 67238407Methyl 4-(bromomethyl)-2-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-6-(3-(trifluoromethyl)phenylamino)pyrimidine-5-carboxylate

Product 2

HCID 6422Trifluoroacetic acidHCID 53251801HCID 53251801, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-(bromomethyl)-2-((1R,2S)-2-(tert-butoxycarbonyl-amino)cyclohexylamino)-6-(3-(trifluoromethyl)phenylamino)pyrimidine-5-carboxylate (120 mg, 0.199 mmol) in THF was treated with ammonium hydroxide. The reaction mixture was stirred at RT overnight, and subsequently worked up and purified by reverse phase preparative HPLC. The fractions were collected and concentrated under reduced pressure to give a residue, which was treated with TFA/DCM. The final product was purified again by preparative HPLC. Lyophilization gave a TFA salt of the title compound as a white solid (2.6 mg, 3%). [M+H] calc'd for C19H21F3N6O, 407; found, 407.

Workup

  1. custompurified by reverse phase preparative HPLC
  2. customThe fractions were collected
  3. concentrationconcentrated under reduced pressure
  4. customto give a residue, which
  5. customThe final product was purified again by preparative HPLC

Sources & evidence

ORD record
ord-e036ac6febd24a818003389875e4b9c7
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

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