Dimethylformamide → HCID 59140918, compound

HRID 737203Notes

Reaction equation

HRID 737203 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(ON1N=[N:48][C:43]2[CH:44]=[CH:45][CH:46]=[N:47][C:42]1=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](N1CCCC(N)C1)=[O:72])([CH3:69])([CH3:68])[CH3:67].CN([CH:83]=[O:84])C>>[C:66]([O:70][C:71]([N:47]1[CH2:46][CH2:45][CH2:44][CH:43]([NH:48][C:83](=[O:84])[C:26]2[CH:27]=[CH:28][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:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[O:10])=[O:32])[S:19][CH:20]=3)=[CH:24][CH:25]=2)[CH2:42]1)=[O:72])([CH3:69])([CH3:68])[CH3:67]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 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 59140918HCID 59140918, compound

Procedure

2-[4-(2-carboxy-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (General Procedure 3A, 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 56.3 mg 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: 634.3 (M+H+); H1 NMR (DMSO-d6): δ(ppm) 12.48 (s, 1H), 8.10 (m, 5H), 7.36 (br s, 2H), 7.08 (m, 3H), 5.01 (m, 2H), 4.43 (m, 2H), 3.80-3.50 (m, 4H), 2.81 (m, 2H), 2.23 (m, 2H), 1.93 (m, 5H), 1.29 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-3b85095d7bfa4b44a2a0fbcb81fb9d17
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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