Diisopropylethylamine → HCID 87499345, compound

HRID 737179Notes

Reaction equation

HRID 737179 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.CN([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[CH2:76][CH:75]([NH2:77])[CH2:74]1)=[O:72])([CH3:69])([CH3:68])[CH3:67]>CN(C=O)C>[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:24]=[CH:25][C:26]([C:36](=[O:40])[NH:77][CH:75]3[CH2:76][N:73]([C:71]([O:70][C:66]([CH3:69])([CH3:67])[CH3:68])=[O:72])[CH2:74]3)=[CH:27][CH:28]=2)[N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 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 87499345HCID 87499345, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[4-(2-Carboxy-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (IS2277-52, 125 mg, 0.28 mmol) 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 48.2 mg (0.28 mmol) of 3-amino-azetidine-1-carboxylic acid tert-butyl ester. Reaction mixture was stirred at room temperature overnight to yield crude 2-{4-[4-(1-tert-butoxycarbonyl-azetidin-3-ylcarbamoyl)-phenyl]-thiazol-2-ylcarbamoyl}-pyrrolodine-1-carboxylic acid benzyl ester, which was then purified using reverse phase HPLC. The purified material was dissolved in 4 mL of 1:1 solution of CH2Cl2/TFA and stirred for 1.5 hours at room temperature. Reaction mixture was evaporated under reduced pressure to give pure desired product. MS: 506.1 (M+H+); H1 NMR (DMSO-d6): δ(ppm) 12.50 (br s, 1H), 8.47 (br s, 1H), 7.91 (m, 5H), 7.10 (m, 4H), 5.31 (br s, 1H), 5.02 (m, 2H), 4.51 (m, 1H), 4.08 (m, 3H), 2.47 (m, 3H), 2.23 (m, 1H), 1.90 (m, 4H), 1.94 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-2f58e1c2c55849199e1ce8575860660f
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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