Triethylamine → HCID 57884165, compound

HRID 1818084Notes

Reaction equation

HRID 1818084 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[N:2]1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([C:23]2([CH2:28][NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C(#N)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([C:23]2([CH2:28][NH:29][C:10]([C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][N:2]=3)=[O:12])[CH2:24][CH2:25][CH2:26][CH2:27]2)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 78250Indazole-3-carboxylic acidHCID 739193STK362959HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 57884165HCID 57884165, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1H-Indazole-3-carboxylic acid (32.4 mg, 0.200 mmol) and C-[1-(3,4-Dimethoxy-phenyl)-cyclopentyl]-methylamine (47.1 g, 0.200 mmol) were dissolved in acetonitrile (1 mL) containing triethylamine (83.6 μL, 0.600 mmol). O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (76.0 mg, 0.200 mmol) was added and the solution was allowed to stir for 16 hours. The mixture was then purified by reverse phase preparative liquid chromatography to yield the pure product (7.47 mg, 0.0197 mmol, 9.84%) ESI-MS m/z calc. 379.2, found 380.4 (M+1)+. Retention time of 3.02 minutes.

Workup

  1. customThe mixture was then purified by reverse phase preparative liquid chromatography

Sources & evidence

ORD record
ord-4abfe7cb665d4851b9355dcb2915821b
Source dataset
uspto-grants-2009_10
Patent number
US07598412B2

Reaction notes

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