Tert-Butylamine → HCID 70913715, compound

HRID 1844733Notes

Reaction equation

HRID 1844733 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([C:11]([OH:13])=O)[CH:8]=[C:7]([C:14]2[N:15]([CH2:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:16]([CH3:23])=[C:17]([S:19](=[O:22])(=[O:21])[NH2:20])[CH:18]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:31]([NH2:35])([CH3:34])([CH3:33])[CH3:32].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.O>[C:31]([NH:35][C:11](=[O:13])[C:9]1[CH:8]=[C:7]([C:14]2[N:15]([CH2:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:16]([CH3:23])=[C:17]([S:19](=[O:21])(=[O:22])[NH2:20])[CH:18]=2)[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[N:10]=1)([CH3:34])([CH3:33])[CH3:32]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70874330HCID 70874330, compound

Product 1

HCID 70913715HCID 70913715, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of compound 19 (150 mg, 0.34 mmol), tert-butylamine (36 mg, 0.48 mmol), HATU (207 mg, 0.54 mmol) and DIPEA (146 mg, 1.14 mmol) in DMF (5 mL) was stirred at rt for 20 min, diluted with water and extracted with EA. The organic layer was washed with brine, dried over Na2SO4, concentrated and purified by CC (PE/EA=2/1) to give compound 20 (46 mg, 30%) as a white powder. 1H-NMR (300 MHz, CDCl3) δ: 8.17 (s, 1H), 7.93 (d, 1H, J=1.5 Hz), 7.40 (d, 1H, J=1.5 Hz), 6.61 (s, 1H), 4.70 (d, 2H, J=5.4 Hz), 3.84 (d, 2H, J=6.9 Hz), 2.55 (s, 3H), 1.61 (m, 3H), 1.50 (s, 9H), 1.42 (s, 9H), 1.30-1.38 (m, 3H), 0.97-1.03 (m, 3H), 0.63 (m, 2H). MS Calcd.: 488; MS Found: 489 (M+1).

Workup

  1. extractionextracted with EA
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by CC (PE/EA=2/1)

Sources & evidence

ORD record
ord-d4fb036e92564b55a8d92786180d4a8b
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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