Diisopropylethylamine → HCID 59140928, compound

HRID 737180Notes

Reaction equation

HRID 737180 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN([C:19]([O:23]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[N:49]1[CH:54]=[CH:53][CH:52]=[C:51]([C:55]2[N:56]=[C:57]([NH2:60])[S:58][CH:59]=2)[CH:50]=1>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:19](=[O:23])[NH:60][C:57]1[S:58][CH:59]=[C:55]([C:51]2[CH:50]=[N:49][CH:54]=[CH:53][CH:52]=2)[N:56]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1548934-(3-Pyridinyl)-2-thiazolamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 106083071-Cbz-pyrrolidine

Product 1

HCID 59140928HCID 59140928, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pyrrolidine-1-carboxylic acid benzyl ester, (224 mg, 0.9 mmol) was combined with 376 mg (1.0 mmol) of HATU. This mixture was dissolved in 15 ml of DMF. To this solution was added DIEA (1.8 mmol, 0.3 mL). This solution was stirred at room temperature for 1.5 hours. To this solution was then added 4-pyridin-3-yl-thiazol-2-ylamine (100 mg, 0.56 mg). Reaction mixture was stirred at room temperature overnight and then purified using reverse phase HPLC. MS: 409.1 (M+H+); H1 NMR (DMSO-d6): δ(ppm) (HCl salt) 12.62 (s, 1H), 9.28 (s, 1H), 8.78 (s, 1H), 8.03 (m, 2H), 7.38 (m, 3H), 7.04 (d, 2H), 5.00 (m, 2H), 4.53 (m, 1H), 3.62 (m, 2H), 2.22 (m, 1H), 1.89 (m, 4H).

Workup

  1. customReaction mixture
  2. stirringwas stirred at room temperature overnight
  3. custompurified

Sources & evidence

ORD record
ord-8d20a0ced70d470d87e668b52970f89b
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

Loading…