Trifluoroacetic acid → HCID 117706766, compound

HRID 1778538Notes

Reaction equation

HRID 1778538 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH2:19][N:20]2[CH:25]3[CH2:26][CH2:27][CH:21]2[CH2:22][N:23]([C:28]([O:30]C(C)(C)C)=O)[CH2:24]3)[NH:12][C:11]([C:35]2[S:36][CH:37]=[CH:38][N:39]=2)=[N:10]1.F[C:41](F)(F)C(O)=O>ClCCl>[C:28]([N:23]1[CH2:24][CH:25]2[N:20]([CH2:19][C:13]3[NH:12][C:11]([C:35]4[S:36][CH:37]=[CH:38][N:39]=4)=[N:10][C@@H:9]([C:3]4[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=4[Cl:1])[C:14]=3[C:15]([O:17][CH3:18])=[O:16])[CH:21]([CH2:27][CH2:26]2)[CH2:22]1)(=[O:30])[CH3:41]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117697538HCID 117697538, compound

Product 1

HCID 117706766HCID 117706766, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 8-[[(4R)-4-(2-chloro-4-fluoro-phenyl)-5-methoxycarbonyl-2-thiazol-2-yl-1,4-dihydropyrimidin-6-yl]methyl]-3,8-diazabicyclo[3.2.1]octane-3-carboxylate (80 mg), trifluoroacetic acid (1.0 mL) and dichloromethane (2.0 mL) was stirred at room temperature for one hour, and then concentrated. The residue was dissolved in dichloromethane (5.0 mL), followed by adding diisopropylethylamine (0.2 mL) and acetic chloride (0.1 mL). The result mixture was stirred at room temperature overnight. The reaction mixture was concentrated and purified by prep-HPLC to give Methyl (4R)-6-[(3-acetyl-3,8-diazabicyclo[3.2.1]octan-8-yl)methyl]-4-(2-chloro-4-fluoro-phenyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate 122 (11.3 mg).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in dichloromethane (5.0 mL)
  3. additionby adding diisopropylethylamine (0.2 mL) and acetic chloride (0.1 mL)
  4. stirringThe result mixture was stirred at room temperature overnight
  5. concentrationThe reaction mixture was concentrated
  6. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-f1072fe1a7364d31901e718e01131eb4
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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