Isobutylamine → HCID 70869208, compound

HRID 1844725Notes

Reaction equation

HRID 1844725 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([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:13]=1)[C:8]([OH:10])=O)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:64][CH:65]([CH3:68])[CH2:66][NH2:67]>CN(C=O)C>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([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:13]=1)[C:8]([NH:67][CH2:66][CH:65]([CH3:68])[CH3:64])=[O:10])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 6558IsobutylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70869080HCID 70869080, compound

Product 1

HCID 70869208HCID 70869208, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of compound 13b (90 mg, 0.21 mmol), DIPEA (134 mg, 1.04 mmol) and HATU (157 mg, 0.41 mmol) in DMF was stirred at rt for 1 h, then 2-methylpropan-1-amine (18 mg, 0.25 mmol) was added. The mixture was stirred at rt overnight and concentrated. The product was isolated by CC to get compound 13 (45 mg, 45%). 1H-NMR (400 MHz, DMSO-d6) δ: 8.57 (m, 1H), 7.85 (s, 1H), 7.67 (s, 1H), 7.52 (s, 1H), 6.94 (s, 2H), 6.39 (s, 1H), 3.82 (d, J=5.6 Hz, 2H), 3.09 (s, 2H), 2.45 (s, 3H), 1.85-1.84 (m, 1H), 1.46 (s, 3H), 1.33-1.25 (m, 12H), 0.94-0.88 (m, 9H), 0.66-0.63 (m, 2H). MS Found: 488 (M+1).

Workup

  1. stirringThe mixture was stirred at rt overnight
  2. concentrationconcentrated
  3. customThe product was isolated by CC

Sources & evidence

ORD record
ord-648b3e06f34b4f6cb8048778abda3e86
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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