Diisopropylethylamine → HCID 86682806, compound

HRID 1504331Notes

Reaction equation

HRID 1504331 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@H:9]2[CH3:21])=[N:6][CH:7]=1.[Br:22][C:23]1[C:31]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][C:24]=1[Cl:37].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[Br:22][C:23]1[C:31]([O:32][C:33]([F:34])([F:35])[F:36])=[CH:30][C:26]([C:27]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@H:9]3[CH3:21])=[N:6][CH:7]=2)=[O:28])=[CH:25][C:24]=1[Cl:37]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67495583HCID 67495583, compoundHCID 86682807HCID 86682807, compound

Product 1

HCID 86682806HCID 86682806, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a mixture of (R)-tert-butyl 4-(5-aminopyridin-2-yl)-3-methylpiperazine-1-carboxylate (59.9 mg, 0.21 mmol) and 4-bromo-3-chloro-5-(trifluoromethoxy)benzoic acid (65.5 mg, 0.21 mmol; Preparation 50) in DMA (0.5 mL) at RT was added HATU (86 mg, 0.23 mmol) followed by DIPEA (0.11 mL, 0.62 mmol). The reaction mixture was stirred at RT for 1 h, partitioned between EtOAc (10 mL) and water (2 mL). The organic layer was washed with water (2 mL), dried over sodium sulfate, filtered and concentrated to give the title intermediate as a dark purplish oil. (m/z): [M+H]+ calcd for C23H25BrClF3N4O4 593.07; 595.07. found 595.

Workup

  1. custompartitioned between EtOAc (10 mL) and water (2 mL)
  2. washThe organic layer was washed with water (2 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3cd9b17cc00942c29f15514159b74aba
Source dataset
uspto-grants-2015_12
Patent number
US09212168B2

Reaction notes

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