Diisopropylethylamine → HCID 59140916, compound

HRID 737178Notes

Reaction equation

HRID 737178 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16](=[O:32])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2C(O)=O)[N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:34]([C:36]([O:40]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:66]([O:70][C:71]([N:73]1[CH2:78][CH2:77][CH2:76][CH:75](N)[CH2:74]1)=[O:72])([CH3:69])([CH3:68])[CH3:67]>CN(C=O)C>[C:66]([O:70][C:71]([N:73]1[CH2:74][CH2:75][CH:76]([NH:34][C:36](=[O:40])[C:26]2[CH:25]=[CH:24][C:23]([C:21]3[N:22]=[C:18]([NH:17][C:16]([CH:12]4[CH2:13][CH2:14][CH2:15][N:11]4[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])=[O:32])[S:19][CH:20]=3)=[CH:28][CH:27]=2)[CH2:77][CH2:78]1)=[O:72])([CH3:67])([CH3:68])[CH3:69]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5458091-BOC-3-AminopiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86616433HCID 86616433, compound

Product 1

HCID 59140916HCID 59140916, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

125 mg (0.28 mmol) of 2-[4-(2-carboxy-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (IS2277-52) was dissolved in 4 mL of DMF. To this solution was added HATU (160.9 mg, 0.42 mmol) and DIEA (0.05 mL, 0.36 mmol). This solution was stirred at room temperature for 1 hour. To this solution was added 56.1 mg (0.28 mmol) of 3-amino-piperidine-1-carboxylic acid tert-butyl ester. Reaction mixture was stirred overnight at room temperature, and then purified using reverse phase HPLC. MS: 634.2 (M+H+); H1 NMR (meOH-d4): δ(ppm) 8.02 (m, 2H), 7.89 (m, 2H), 7.58 (m, 1H), 7.39 (m, 3H), 7.19 (m, 1H), 7.07 (m, 2H), 5.03 (m, 2H), 45.2 (m, 1H), 4.11 (m, 3H), 3.61 (m, 4H), 3.19 (m, 1H), 2.97 (m, 2H), 2.41 (m, 1H), 2.28 (m, 1H), 2.01 (m, 4H), 1.48 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-ae6748be0678420bbe453714711a74c4
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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