Diisopropylethylamine → HCID 178455430, compound

HRID 1982937Notes

Reaction equation

HRID 1982937 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]([OH:13])=O)=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.[C:14]([SiH2:18][O:19][C:20]([CH3:30])([CH3:29])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH2:27])[C:22]=1[NH2:28])([CH3:17])([CH3:16])[CH3:15].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>CN(C=O)C>[NH2:28][C:22]1[C:21]([C:20]([CH3:30])([CH3:29])[O:19][SiH2:18][C:14]([CH3:16])([CH3:15])[CH3:17])=[CH:26][CH:25]=[CH:24][C:23]=1[NH:27][C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[NH:8][N:9]=1)=[O:13]

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 1317274553-(Tert-butyl-dimethyl-silanyloxymethyl)-benzene-1,2-diamineHCID 178524942HCID 178524942, compound

Product 1

HCID 178455430HCID 178455430, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid Compound 1c (1.0 g, 4.13 mmol) and 3-(tert-butyl-dimethyl-silanyloxymethyl)-benzene-1,2-diamine Compound 6a (1.05 g, 4.17 mmol), HATU (1.58 g, 4.16 mmol) and DIPEA (2.5 mL, 35.9 mmol) in DMF (50 mL) was stirred at room temperature overnight. The solvent was removed and the residue was dissolved in ethyl acetate (100 mL), then sequentially washed with hydrochloric acid (20 mL, 1M), water (30 mL×3) and brine (20 mL). The organic solution was evaporated to dryness in vacuo and purified by silica gel chromatography (10% to 50% of ethyl acetate in hexanes) to yield 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid [2-amino-3-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-amide Compound 6b (1.21 g, 61% yield) as a yellow powder. 1H NMR (300 MHz, CDCl3) δ 8.91 (d, 1H, J=2.1 Hz), 8.73 (s, 1H), 8.67 (d, 1H, J=2.1 Hz), 7.47 (d, 1H, J=7.2 Hz), 7.01 (d, 1H, J=7.2 Hz), 6.83 (t, 1H, J=7.2 Hz), 4.78 (s, 2H), 0.95 (s; 9H), 0.11 (s, 6H); MS (ESI) m/z: 477 (M+H+).

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  3. washsequentially washed with hydrochloric acid (20 mL, 1M), water (30 mL×3) and brine (20 mL)
  4. customThe organic solution was evaporated to dryness in vacuo
  5. custompurified by silica gel chromatography (10% to 50% of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c2755b97a4954d9dabe9b25ed24ca4a7
Source dataset
uspto-grants-2009_06
Patent number
US07541367B2

Reaction notes

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