Diisopropylethylamine → HCID 25099694, compound

HRID 2381948Notes

Reaction equation

HRID 2381948 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=1.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.[NH2:50][N:51]1[C:59]2[C:54](=[CH:55][C:56]([F:60])=[CH:57][CH:58]=2)[C:53]([CH2:61][C:62]([CH3:65])([OH:64])[CH3:63])=[CH:52]1>CN(C=O)C.CCOC(C)=O>[F:60][C:56]1[CH:55]=[C:54]2[C:59](=[CH:58][CH:57]=1)[N:51]([NH:50][C:8]([C:7]1[C:2]([CH3:1])=[N:3][C:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[N:5][CH:6]=1)=[O:10])[CH:52]=[C:53]2[CH2:61][C:62]([OH:64])([CH3:63])[CH3:65]

Participants

7

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 617020254-Methyl-2-(pyridin-2-yl)pyrimidine-5-carboxylic acidHCID 68555047HCID 68555047, compound

Product 1

HCID 25099694HCID 25099694, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (748 mg, 3.48 mmol) in DMF (30 mL) is treated with HATU (1.3 g, 3.48 mmol) and DIPEA (1.2 mL, 6.96 mmol), and the mixture is stirred at rt for 30 min. 1-(1-Amino-5-fluoroindol-3-yl)-2-methyl-propan-2-ol (2.9 mmol) is added and the mixture is stirred at 80° C. for 12 h. The mixture is diluted with EtOAc, washed with saturated aqueous NH4Cl and saturated aqueous Na2CO3, dried (Na2SO4), filtered and concentrated in vacuo to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid [5-fluoro-3-(2-hydroxy-2-methyl-propyl)-indol-1-yl]-amide (990 mg, 81%). MS: 420 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 1.13 (s, 6H), 2.75 (s, 2H), 2.85 (s, 3H), 6.84 (m, 1H), 7.24 (m, 1H), 7.37 (m, 1H), 7.53 (m, 1H), 7.95 (s, 1H), 7.98 (m, 1H), 8.44 (m, 1H), 8.76 (m, 1H), 9.15 (s, 1H).

Workup

  1. stirringthe mixture is stirred at 80° C. for 12 h
  2. washwashed with saturated aqueous NH4Cl and saturated aqueous Na2CO3
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98a5e3a46500424f96b89eef034916ff
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

Loading…